Diamide invertebrate pest control agents containing a non-aromatic heterocyclic ring

ABSTRACT

This invention provides compounds of Formula I, their N-oxides and agriculturally suitable salts wherein A and B are independently O or S; J is an optionally substituted 5- or 6-memebered nonaromatic heterocyclic ring; K is taken together with the two contiguous linking carbon atoms to form a phenyl ring or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted; and R 1 , R 2 , and R 3  are as defined in the disclosure. Also disclosed are methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula I, an N-oxide thereof or a suitable salt of the compound (e.g., as a composition described herein). This invention also pertains to a composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of Formula I, an N-oxide thereof or a suitable salt of the compound and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.

BACKGROUND OF THE INVENTION

[0001] This invention relates to certain heterocyclic diamides, theirN-oxides, suitable salts and compositions, and a method of their use forcontrolling invertebrate pests in both agronomic and nonagronomicenvironments.

[0002] The control of invertebrate pests is extremely important inachieving high crop efficiency. Damage by invertebrate pests to growingand stored agronomic crops can cause significant reduction inproductivity and thereby result in increased costs to the consumer. Thecontrol of invertebrate pests in forestry, greenhouse crops,ornamentals, nursery crops, stored food and fiber products, livestock,household, and public and animal health is also important. Many productsare commercially available for these purposes, but the need continuesfor new compounds that are more effective, less costly, less toxic,environmentally safer or have different modes of action.

[0003] NL 9202078 discloses N-acyl anthranilic acid derivatives ofFormula i as insecticides

[0004] wherein, inter alia, X is a direct bond; Y is H or C₁-C₆ alkyl; Zis NH₂, NH(C₁-C₃ alkyl) or N(C₁-C₃ alkyl)₂; and R¹ through R⁹ areindependently H, halogen, C₁-C₆ alkyl, phenyl, hydroxy, C₁-C₆ alkoxy orC₁-C₇ acyloxy.

[0005] WO01/070671 discloses N-acyl anthranilic acid derivatives ofFormula ii as arthropodicides

[0006] wherein, inter alia, A and B are independently O or S; J is anoptionally substituted phenyl ring, 5- or 6-membered heteroaromaticring, naphthyl ring system or an aromatic 8-, 9- or 10-membered fusedheterobicyclic ring system; R¹ and R³ are independently H or optionallysubstituted C₁-C₆ alkyl; R² is H or C₁-C₆ alkyl; each R⁴ isindependently H, C₁-C₆ alkyl C₁-C₆ haloalkyl, halogen or CN; and n is 1to 4.

SUMMARY OF TIE INVENTION

[0007] This invention pertains to compounds of Formula I, and N-oxidesor agriculturally suitable salts thereof

[0008] wherein

[0009] A and B are independently O or S;

[0010] J is an optionally substituted 5- or 6-membered nonaromaticheterocyclic ring;

[0011] K is taken together with the two contiguous linking carbon atomsto form a phenyl ring or a 5- or 6-membered heteroaromatic ring, eachring optionally substituted;

[0012] R¹ is H; C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆cycloalkyl, optionally substituted; C₂-C₆ alkylcarbonyl; C₂-C₆alkoxycarbonyl; C₂-C₆ alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl;

[0013] R² is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆cycloalkyl, C₁-C₄ alkoxy, C_(l)-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl;

[0014] R³ is H; G; C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆cycloalkyl, each optionally substituted; or

[0015] R² and R³ can be taken together with the nitrogen to which theyare attached to form a ring containing 2 to 6 atoms of carbon andoptionally one additional atom of nitrogen, sulfur or oxygen, and saidring may be optionally substituted; and

[0016] G is an optionally substituted 5- or 6-membered nonaromaticcarbocyclic or heterocyclic ring, optionally including one or two ringmembers selected from the group consisting of C(═O), SO or S(O)₂.

[0017] This invention also pertains to a method for controlling aninvertebrate pest comprising contacting the invertebrate pest or itsenvironment with a biologically effective amount of a compound ofFormula I, an N-oxide thereof or a suitable salt of the compound (e.g.,as a composition described herein). This invention also relates to sucha method wherein the invertebrate pest or its environment is contactedwith a biologically effective amount of a compound of Formula I, anN-oxide thereof or a suitable salt thereof, or a composition comprisingthe compound, N-oxide thereof or a suitable salt thereof and abiologically effective amount of at least one additional compound oragent for controlling an invertebrate pest.

[0018] This invention also pertains to a composition for controlling aninvertebrate pest comprising a biologically effective amount of acompound of Formula I, an N-oxide thereof or a suitable salt of thecompound and at least one additional component selected from the groupconsisting of surfactants, solid diluents and liquid diluents. Thisinvention also pertains to a composition comprising a biologicallyeffective amount of a compound of Formula I, an N-oxide thereof or asuitable salt of the compound and an effective amount of at least oneadditional biologically active compound or agent.

DETAILS OF THE INVENTION

[0019] As noted above, J is an optionally substituted 5- or 6-memberednonaromatic heterocyclic ring. The term “optionally substituted” inconnection with these J groups refers to J groups which areunsubstituted or have at least one non-hydrogen substituent that doesnot extinguish the biological activity. Examples of optionallysubstituted J groups wherein said rings are optionally substituted withfrom one to seven R⁵ include the rings illustrated in Exhibit 1, whereinm is an integer from 1 to 7 and R⁵ is as defined below. As with thecarbon atoms in the ring, the nitrogen atoms that require substitutionto fill their valence are substituted with hydrogen or with R⁵. Although(R⁵)_(m) groups are shown in the structures J-1 to J-35, it is notedthat R⁵ does not need to be present since it is an optional substituent.It is also noted that when the R⁵ substituent is H, that is equivalentto the atom to which the R⁵ substituent is attached as beingunsubstituted. Note that when the attachment point on the J group isillustrated as floating, the J group can be attached to the remainder ofFormula I through any available carbon or nitrogen atom of the J groupby replacement of a hydrogen atom. Note that J-3 and J-4 are subsets ofJ-19 in which the attachment point to the rest of Formula I is fixed.Note that in J-5, X is O or S, and that when X is O, J-5 is a subset ofJ-29 in which the attachment point to the rest of Formula I is fixed,and that when X is S, J-5 is a subset of J-30 in which the attachmentpoint to the rest of Formula I is fixed. Preferred attachment points ofJ-17 and J-22 are at the positions indicated as 4 or 5 of the oxazolineJ-17 and thiazoline J-22.

[0020] Examples of optional R⁵ substituents when attached to J includethose wherein

[0021] each R⁵ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂,hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl,C₃-C₆ trialkylsilyl or W;

[0022] (R₅)₂ when attached to adjacent carbon atoms can be takentogether as —OCF₂O—, —CF₂CF₂O—, or —OCF₂CF₂O—; and

[0023] each W is independently a phenyl, benzyl, benzoyl, phenoxy, 5- or6-membered heteroaromatic ring, a naphthyl ring system or an aromatic8-, 9- or 10-membered fused heterobicyclic ring system, each ring orring system optionally substituted with from one to three substituentsindependently selected from the group consisting of C₁-C₄ alkyl, C₂-C₄alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂,C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl,C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl,C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈dialkylaminocarbonyl or C₃-C₆ trialkylsilyl.

[0024] As noted above, K is taken together with the two contiguouslinking carbon atoms to form a phenyl ring or a 5- or 6-memberedheteroaromatic ring, each ring optionally substituted. The term“optionally substituted” in connection with these K groups refers to Kgroups that are unsubstituted or have at least one non-hydrogensubstituent that does not extinguish the biological activity. Examplesof optionally substituted phenyl rings (K-38) and aromatic heterocyclicrings (K-1 to K-37) wherein said rings are optionally substituted withfrom 1 to 4 R⁴ include the ring systems illustrated in Exhibit 2,wherein n is an integer from 1 to 4 and R⁴ is as defined below. As withthe carbon atoms in the ring, the nitrogen atoms that requiresubstitution to fill their valence are substituted with hydrogen or withR⁴. Although (R⁴)_(n) groups are shown in the structures K-1 to K-38, itis noted that R⁴ does not need to be present since it is an optionalsubstituent. Note that some K groups can only be substituted with lessthan 3 R⁴ groups (e.g. K-7 through K-10, K-15, K-16, K-20, K-21, K-23,K-24, K-26 and K-27 can only be substituted with one R⁴). In theexemplified K groups, the upper right bond is attached through theavailable linking carbon atom to the nitrogen atom of the NR¹(═A)Jportion of Formula I and the lower right bond is attached through theavailable linking carbon atom to the carbon atom of the C(═B)NR²R³portion of Formula I. The wavy line indicates that the K ring isattached to the remainder of Formula I as illustrated below in FormulaIa.

[0025] Preferred K rings include optionally substituted thiophene,isoxazole, isothiazole, pyrazole, pyridine, pyrimidine and phenyl rings.More preferred K rings include K-1, K-14, K-15, K-18, K-23, K-28, K-29,K-30, K-31, K33 and K-38. Most preferred K rings are K-28 K-31, K-33 andK-38.

[0026] Examples of optional R⁴ substituents when attached to K includethose wherein each R⁴ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl,C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, hydroxy,C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl,C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, NH₂, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, or C₃-C₆ trialkylsilyl; or

[0027] each R⁴ is independently phenyl, benzyl or phenoxy, eachoptionally substituted with from one to three substituents selected fromthe group consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino,C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino,C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl,C₃-C₈ dialkylaminocarbonyl and C₃-C₆ trialkylsilyl.

[0028] As noted above, R¹ is (among others) C₁-C₆ alkyl, C₂-C₆ alkenyl,C₂-C₆ alkynyl or C₃-C₆ cycloalkyl, each optionally substituted. The term“optionally substituted” in connection with these R¹ groups refers to R¹groups that are unsubstituted or have at least one non-hydrogensubstituent that does not extinguish the biological activity. Examplesof optionally substituted R¹ groups include those optionally substitutedwith one or more substituents independently selected from the groupconsisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio,C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₁-C₄alkylamino, C₂-C₈ dialkylamino and C₃-C₆ cycloalkylamino. Of note are R¹groups optionally substituted with from one to five substituentsindependently selected from the group above.

[0029] As noted above, R³ is (among others) C₁-C₆ alkyl, C₂-C₆ alkenyl,C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, each optionally substituted. The term“optionally substituted” in connection with these R³ groups refers to R³groups that are unsubstituted or have at least one non-hydrogensubstituent that does not extinguish the biological activity. Examplesof optionally substituted R³ groups include those optionally substitutedwith one or more substituents selected from the group consisting ofhalogen, G, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₆alkoxycarbonyl, C₂-C₆ alkylcarbonyl, C₃-C₆ trialkylsilyl, or a phenyl,phenoxy or 5- or 6-membered heteroaromatic ring, each ring optionallysubstituted with from one to three substituents independently selectedfrom R⁶; C₁-C₄ alkylamino; C₂-C₈ dialkylamino; C₃-C₆ cycloalkylamino;C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl. Of note are R³ groupsoptionally substituted with from one to five substituents independentlyselected from the group above.

[0030] As noted above, R² and R³ can be taken together with the nitrogento which they are attached to form a ring containing 2 to 6 atoms ofcarbon and optionally one additional atom of nitrogen, sulfur or oxygen,and said ring may be optionally substituted. The term “optionallysubstituted” in connection with said rings refers to rings that areunsubstituted or have at least one non-hydrogen substituent that doesnot extinguish the biological activity. Examples of such optionallysubstituted rings include those optionally substituted with from 1 to 4substituents independently selected from R⁷ wherein each R⁷ isindependently C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂ alkoxy.

[0031] As noted above, G is a 5- or 6-membered nonaromatic carbocyclicor heterocyclic ring, optionally including one or two ring membersselected from the group consisting of C(═O), SO or S(O)₂ and optionallysubstituted with 1 to 4 substituents selected from the group consistingof C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂ alkoxy. The term “optionallysubstituted” in connection with these G groups refers to groups whichare unsubstituted or have at least one non-hydrogen substituent thatdoes not extinguish the arthropodicidal activity possessed by theunsubstituted analog. Note that when the attachment point on the G groupis illustrated as floating, the G group can be attached to the remainderof Formula I through any available carbon of the G group by replacementof a hydrogen atom. The optional substituents can be attached to anyavailable carbon by replacing a hydrogen atom. Examples of 5- or6-membered nonaromatic carbocyclic rings as G include the ringsillustrated as G-1 through G-8 of Exhibit 3, wherein such rings areoptionally substituted with 1 to 4 substituents selected from the groupconsisting of C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂ alkoxy. Examplesof 5- or 6-membered nonaromatic heterocyclic rings as G include therings illustrated as G-9 through G-38 of Exhibit 3, wherein such ringsare optionally substituted with 1 to 4 substituents selected from thegroup consisting of C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂ alkoxy. Notethat when G comprises a ring selected from G-31 through G-34, G-37 andG-38, Q¹ is selected from O, S or N. Note that when G is G-11, G13,G-14, G16, G-23, G-24, G-30 through G-34, G-37 and G-38 and Q¹ is N, thenitrogen atom can complete its valence by substitution with either H orC₁-C₂ alkyl.

[0032] In the above recitations, “aromatic” indicates that each of thering atoms is essentially in the same plane and has a p-orbitalperpendicular to the ring plane, and in which (4n+2)π electrons, when nis 0 or a positive integer, are associated with the ring to comply withHückel's rule. The term “aromatic ring system” denotes fully unsaturatedcarbocycles and heterocycles in which at least one ring of a polycyclicring system is aromatic. Aromatic carbocyclic ring or ring systemsincludes fully aromatic carbocycles and carbocycles in which at leastone ring of a polycyclic ring system is aromatic (e.g. phenyl andnaphthyl). The term “nonaromatic carbocyclic ring” denotes fillysaturated carbocycles as well as partially or fully unsaturatedcarbocycles where the Hückel rule is not satisfied by the ring. The term“hetero” in connection with rings or ring systems refers to a ring orring system in which at least one ring atom is not carbon and which cancontain 1 to 4 heteroatoms independently selected from the groupconsisting of nitrogen, oxygen and sulfur, provided that each ringcontains no more than 4 nitrogens, no more than 2 oxygens and no morethan 2 sulfurs. The terms “heteroaromatic ring or ring system” and“aromatic fused heterobicyclic ring system” includes fully aromaticheterocycles and heterocycles in which at least one ring of a polycyclicring system is aromatic (where aromatic indicates that the Hückel ruleis satisfied). The term “nonaromatic heterocyclic ring or ring system”denotes fully saturated heterocycles as well as partially or fullyunsaturated heterocycles where the Hückel rule is not satisfied by anyof the rings in the ring system. The heterocyclic ring or ring systemcan be attached through any available carbon or nitrogen by replacementof a hydrogen on said carbon or nitrogen.

[0033] The term “alkyl”, used either alone or in compound words such as“alkylthio” or “haloalkyl” includes straight-chain or branched alkyl,such as methyl, ethyl, n-propyl, i-propyl, or the different butyl,pentyl or hexyl isomers. “Alkenyl” includes straight-chain or branchedalkenes such as 1-propenyl, 2-propenyl, and the different butenyl,pentenyl and hexenyl isomers. “Alkenyl” also includes polyenes such as1,2-propadienyl and 2,4-hexadienyl. “Alkynyl” includes straight-chain orbranched alkynes such as 1-propynyl, 2-propynyl and the differentbutynyl, pentynyl and hexynyl isomers. “Alkynyl” can also includemoieties comprised of multiple triple bonds such as 2,5-hexadiynyl.“Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy,isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.“Alkylthio” includes branched or straight-chain alkylthio moieties suchas methylthio, ethylthio, and the different propylthio and butylthioisomers. “Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl,cyclopentyl and cyclohexyl.

[0034] The term “halogen”, either alone or in compound words such as“haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as “haloalkyl”, said alkyl may bepartially or fully substituted with halogen atoms which may be the sameor different. Examples of “haloalkyl” include F₃C, ClCH₂, CF₃CH₂ andCF₃CCl₂. The terms “haloalkenyl”, “haloalkynyl”, “haloalkoxy”, and thelike, are defined analogously to the term “haloalkyl”. Examples of“haloalkenyl” include (Cl)₂C═CHCH₂ and CF₃CH₂CH═CHCH₂. Examples of“haloalkynyl” include HC≡CCHCl, CF₃C≡C, CCl₃C≡C and FCH₂C≡CCH₂. Examplesof “haloalkoxy” include CF₃O, CCl₃CH₂O, HCF₂CH₂CH₂O and CF₃CH₂O.

[0035] Examples of “alkylcarbonyl” include C(O)CH₃, C(O)CH₂CH₂CH₃ andC(O)CH(CH₃)₂. Examples of “alkoxycarbonyl” include CH₃OC(═O),CH₃CH₂OC(═O), CH₃CH₂CH₂OC(═O), (CH₃)₂CHOC(═O) and the different butoxy-or pentoxycarbonyl isomers. Examples of “alkylaminocarbonyl” includeCH₃NHC(═O), CH₃CH₂NHC(═O), CH₃CH₂CH₂NHC(═O), (CH₃)₂CHNHC(═O) and thedifferent butylamino- or pentylaminocarbonyl isomers. Examples of“dialkylaminocarbonyl” include (CH₃)₂NC(═O), (CH₃CH₂)₂NC(═O),CH₃CH₂(CH₃)NC(═O), CH₃CH₂CH₂(CH₃)NC(═O) and (CH₃)₂CHN(CH3)C(═O).

[0036] The total number of carbon atoms in a substituent group isindicated by the “C_(i)-C_(j)” prefix where i and j are numbers from 1to 6. For example, C₁-C₃ alkylsulfonyl designates methylsulfonyl throughpropylsulfonyl; C₂ alkoxyalkyl designates CH₃OCH₂.

[0037] In the above recitations, when a compound of Formula I contains aheterocyclic ring, all substituents are attached to this ring throughany available carbon or nitrogen by replacement of a hydrogen on saidcarbon or nitrogen.

[0038] When a group contains a substituent which can be hydrogen, forexample R³, then, when this substituent is taken as hydrogen, it isrecognized that this is equivalent to said group being unsubstituted.

[0039] When a compound is substituted with a substituent bearing asubscript that indicates the number of said substituents can exceed 1,said substituents (when they exceed 1) are independently selected fromthe group of defined substituents. Further, when the subscript indicatesa range, e.g. (R)_(i-j), then the number of substituents maybe selectedfrom the integers between i and j inclusive.

[0040] The term “optionally substituted with from one to threesubstituents” and the like indicates that from one to three of theavailable positions on the group may be substituted. When a groupcontains a substituent which can be hydrogen, for example R¹ or R⁵,then, when this substituent is taken as hydrogen, it is recognized thatthis is equivalent to said group being unsubstituted.

[0041] Compounds of this invention can exist as one or morestereoisomers. The various stereoisomers include enantiomers,diastereomers, atropisomers and geometric isomers. One skilled in theart will appreciate that one stereoisomer may be more active and/or mayexhibit beneficial effects when enriched relative to the otherstereoisomer(s) or when separated from the other stereoisomer(s).Additionally, the skilled artisan knows how to separate, enrich, and/orto selectively prepare said stereoisomers. Accordingly, the compounds ofthe invention may be present as a mixture of stereoisomers, individualstereoisomers, or as an optically active form.

[0042] The present invention comprises compounds selected from FormulaI, N-oxides and agriculturally suitable salts thereof. One skilled inthe art will appreciate that not all nitrogen containing heterocyclescan form N-oxides since the nitrogen requires an available lone pair foroxidation to the oxide; one skilled in the art will recognize thosenitrogen containing heterocycles which can form N-oxides. One skilled inthe art will also recognize that tertiary amines can form N-oxides.Synthetic methods for the preparation of N-oxides of heterocycles andtertiary amines are very well known by one skilled in the art includingthe oxidation of heterocycles and tertiary amines with peroxy acids suchas peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide,alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate,and dioxiranes such as dimethydioxirane. These methods for thepreparation of N-oxides have been extensively described and reviewed inthe literature, see for example: T. L. Gilchrist in ComprehensiveOrganic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press;M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol.3, pp 18-19, A. S. Boulton and A. McKillop, Eds., Pergamon Press; M. R.Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol.43, pp 139-151, A. R. Katritzky, Ed., Academic Press; M. Tisler and B.Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A.R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H.Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry,vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., AcademicPress.

[0043] The salts of the compounds of the invention include acid-additionsalts with inorganic or organic acids such as hydrobromic, hydrochloric,nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic,malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic orvaleric acids. The salts of the compounds of the invention also includethose formed with organic bases (e.g., pyridine, ammonia, ortriethylamine) or inorganic bases (e.g., hydrides, hydroxides, orcarbonates of sodium, potassium, lithium, calcium, magnesium or barium)when the compound contains an acidic group such as a carboxylic acid orphenol.

[0044] Preferred compounds for reasons of cost, ease of synthesis and/orbiological efficacy are:

[0045] Preferred 1. Compounds of Formula I illustrated as Formula Ia

[0046] wherein

[0047] A and B are independently O or S;

[0048] K is taken together with the two linking atoms to form a phenylring or a 5- or 6-membered heteroaromatic ring, each ring optionallysubstituted with from 1 to 4 R⁴;

[0049] X is O or S;

[0050] R¹ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆cycloalkyl each optionally substituted with one or more substituentsindependently selected from the group consisting of halogen, CN, NO₂,hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄alkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈dialkylamino and C₃-C₆ cycloalkylamino; or

[0051] R¹ is C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl;

[0052] R² is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆cycloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl;

[0053] R³ is H; G; C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆cycloalkyl, each optionally substituted with one or more substituentsindependently selected from the group consisting of halogen, G, CN, NO₂,hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆alkylcarbonyl, C₃-C₆ trialkylsilyl, or a phenyl, phenoxy or 5- or6-membered heteroaromatic ring, each ring optionally substituted withfrom one to three substituents selected from R⁶; C₁-C₄ alkylamino; C₂-C₈dialkylamino; C₃-C₆ cycloalkylamino; C₂-C₆ alkoxycarbonyl or C₂-C₆alkylcarbonyl; or

[0054] R² and R³ can be taken together with the nitrogen to which theyare attached to form a ring containing 2 to 6 atoms of carbon andoptionally one additional atom of nitrogen, sulfur or oxygen, said ringmay be optionally substituted with from 1 to 4 substituents selectedfrom R⁷;

[0055] G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclicring, optionally including one or two ring members selected from thegroup consisting of C(═O), SO or S(O)₂ and optionally substituted withfrom 1 to 4 substituents selected from R⁷;

[0056] each R⁴ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, hydroxy, C₁-C₄alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, NH₂, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, or C₃-C₆ trialkylsilyl; or

[0057] each R⁴ is independently phenyl, benzyl or phenoxy, eachoptionally substituted with from one to three substituents selected fromR⁶;

[0058] each R⁵ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂,hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl,C₃-C₆ trialkylsilyl or W;

[0059] (R₅)₂ when attached to adjacent carbon atoms can be takentogether as —OCF₂O—, —CF₂CF₂O—, or —OCF₂CF₂O—;

[0060] each W is independently a phenyl, benzyl, benzoyl, phenoxy, 5- or6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-memberedfused heterobicyclic ring system, each ring optionally substituted withfrom one to three substituents selected from R⁶;

[0061] each R⁶ is independently C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl,C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆(alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl;

[0062] each R⁷ is independently C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂alkoxy,

[0063] m is an integer from 1 to 7; and

[0064] n is an integer from 1 to 3.

[0065] Preferred 2. Compounds of Preferred 1 wherein K is taken togetherwith the two linking atoms to form a phenyl ring optionally substitutedwith from 1 to 3 R⁴.

[0066] Preferred 3. Compounds of Preferred 1 wherein K is taken togetherwith the two linking atoms to form a thiophene, pyrazole, isoxazole,pyridine or pyrimidine optionally substituted with from 1 to 3 R⁴.

[0067] Preferred 4. Compounds of Preferred 2 or Preferred 3 wherein

[0068] A and B are both O;

[0069] n is 1 or 2;

[0070] R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;

[0071] R² is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆cycloalkyl, C₂-C₆alkylcarbonyl or C₂-C₆ alkoxycarbonyl;

[0072] R³ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆cycloalkyl each optionally substituted with one or more substituentsselected from the group consisting of halogen, CN, C₁-C₂ alkoxy, C₁-C₂alkylthio, C₁-C₂ alkylsulfinyl and C₁-C₂ alkylsulfonyl;

[0073] one of the R⁴ groups is attached to the K ring at one of the twopositions ortho to the two linking atoms, and said R⁴ is C₁-C₄ alkyl,C₁-C₄ haloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄haloalkylthio, C₁-C₄ haloalkylsulfinyl or C₁-C₄ haloalkylsulfonyl;

[0074] each R⁵ is independently H, C₁-C₄ alkyl, C₁-C₄ haloalkyl,halogen, CN, NO₂, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl or C₂-C₄ alkoxycarbonyl; andone R⁵ is optionally W; and

[0075] W is a phenyl ring or a 5- or 6-membered heteroaromatic ring,each ring optionally substituted with one to three substituentsindependently selected from R⁶.

[0076] More preferred W groups can be independently phenyl, pyrazole,imidazole, triazole, pyridine or pyrimidine, each ring optionallysubstituted with from one to three substituents independently selectedfrom the group consisting of C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy,C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄alkylsulfonyl, halogen or CN. Examples of such preferred W groupsinclude the rings illustrated as rings W-1 through W-19 illustrated inExhibit 4, wherein each R⁶ is selected from the group consisting ofC₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄allylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, halogen and CN andq is an integer from 1 to 3. As with the carbon atoms in the ring, thenitrogen atoms that require substitution to fill their valence aresubstituted with hydrogen or with R⁶. Although (R⁶)_(q) groups are shownin the structures W-1 through W-19, it is noted that R⁶ does not need tobe present since it is an optional substituent. Note that some W groupscan only be substituted with less than 3 R⁶ groups (e.g. W-5, W-6, W-10,W-12 and W-13 can be substituted with no more than two R⁶). Note that anR⁶ may be attached to any available carbon or nitrogen atom of the Wgroup by replacement of a hydrogen atom. Particularly preferred W groupsinclude W-1 and W-14.

[0077] Preferred 5. Compounds of Preferred 4 wherein

[0078] R¹ is H;

[0079] R²is H or CH₃;

[0080] R³ is H; or C₁-C₄ alkyl, C₁-C₄ alkenyl or C₁-C₄ alkynyl, eachoptionally substituted with halogen, CN, OCH₃, S(O)_(p)CH₃;

[0081] each R⁴ is independently CH₃, CF₃, CN or halogen, and one R⁴group is attached to the K ring at the atom adjacent to the NR¹C(═A)Jmoiety;

[0082] R⁵ is H, C₁-C₄ alkyl, C₁-C₄ haloalkyl, or W;

[0083] W is

[0084] V is N, CH, CF, CCl, CBr or CI;

[0085] each R⁶ and R⁸ is independently H, C₁-C₆ alkyl, C₃-C₆ cycloalkyl,C₁-C₆ haloalkyl, halogen, CN, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy or C₁-C₄haloalkylthio;

[0086] m is 1 or 2; and

[0087] p is 0, 1 or 2.

[0088] Note that J-36 is a subset of J-1 and R⁸ is a subset of R⁵.

[0089] Preferred 6. Compounds of Preferred 5 wherein V is N.

[0090] Preferred 7. Compounds of Preferred 5 wherein V is CH, CF, CCl orCBr.

[0091] Preferred 8. Compounds of Preferred 4 wherein

[0092] J is J-37;

[0093] R¹ is H;

[0094] R² is H or CH₃;

[0095] R³ is H; or C₁-C₄ alkyl, C₁-C₄ alkenyl or C₁-C₄ alkynyl, eachoptionally substituted with halogen, CN, OCH₃, S(O)_(p)CH₃;

[0096] each R⁴ is independently CH₃, CF₃, CN or halogen, and one R⁴group is attached to the K ring at the atom adjacent to the NR¹C(═A)Jmoiety;

[0097] R⁵ is H, C₁-C₄ alkyl, C₁-C₄ haloalkyl, or W;

[0098] W is

[0099] V is N, CH, CF, CCl, CBr or CI;

[0100] R⁶ is independently H, C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₁-C₆haloalkyl, halogen, CN, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy or C₁-C₄haloalkylthio;

[0101] R⁹ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆haloalkenyl, C₃-C₆ alkynyl or C₃-C₆ haloalkynyl;

[0102] m is 1 or 2; and

[0103] p is 0, 1 or2.

[0104] Note that J-37 is a subset of J-2 and R⁹ is a subset of R⁵.

[0105] Most preferred is the compound of Formula 1 selected from thegroup consisting of

[0106]1-(2-Chlorophenyl)-4,5-dihydro-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-trifluoromethyl)-1H-pyrazole-5-carboxamide,

[0107] Methyl1-(2-chlorophenyl)-4,5-dihydro-5-[[[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]amino]carbonyl]1H-pyrazole-3-carboxylate,

[0108] Methyl4,5-dihydro-5-[[[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]amino]carbonyl]-1-(2-methylphenyl)-1H-pyrazole-3-carboxylate,

[0109]4,5-Dihydro-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(2-methylphenyl)-3-(trifluormethyl)-1H-pyrazole-5-carboxamide,

[0110]1-(2-Fluorophenyl)-4,5-dihydro-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

[0111]N-[2-[[(1-Dimethylethyl)amino]carbonyl]-6-methylphenyl]-4,5-dihydro-1-(2-methylphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,and

[0112] 1-(2,6-Difluorophenyl)-4,5-dihydro-N-[2-methyl-6-[[1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide.

[0113] This invention also pertains to a composition for controlling aninvertebrate pest comprising a biologically effective amount of acompound of Formula I, an N-oxide thereof or a suitable salt thereof andat least one additional component selected from the group consisting ofsurfactants, solid diluents and liquid diluents. This invention alsopertains to a composition comprising a biologically effective amount ofa compound of Formula I, an N-oxide thereof or a suitable salt thereofand an effective amount of at least one additional biologically activecompound or agent. The preferred compositions of the present inventionare those which comprise the above preferred compounds.

[0114] This invention also pertains to a method for controlling aninvertebrate pest comprising contacting the invertebrate pest or itsenvironment with a biologically effective amount of a compound ofFormula I, an N-oxide thereof or a suitable salt thereof (e.g., as acomposition described herein). This invention also relates to such amethod wherein the invertebrate pest or its environment is contactedwith a biologically effective amount of a compound of Formula I, anN-oxide thereof or a suitable salt thereof, or a composition comprisingthe compound, N-oxide thereof or a suitable salt thereof and abiologically effective amount of at least one additional compound oragent for controlling an invertebrate pest. The preferred methods of useare those involving the above preferred compounds.

[0115] Of note are compounds of Formula I, and N-oxides oragriculturally suitable salts thereof

[0116] wherein

[0117] A and B are independently O or S;

[0118] J is an optionally substituted 5- or 6-membered nonaromaticheterocyclic ring;

[0119] K is taken together with the two contiguous linking carbon atomsto form a phenyl ring or a 5- or 6-membered heteroaromatic ring, eachring optionally substituted;

[0120] R¹ is H; C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆cycloalkyl, each optionally substituted; C₂-C₆ alkylcarbonyl; C₂-C₆alkoxycarbonyl; C₂-C₆ alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl;

[0121] R² is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆cycloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl;

[0122] R³ is H; G; C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆cycloalkyl, each optionally substituted; or

[0123] R² and R³ can be taken together with the nitrogen to which theyare attached to form a ring containing 2 to 6 atoms of carbon andoptionally one additional atom of nitrogen, sulfur or oxygen, and saidring may be optionally substituted; and

[0124] G is an optionally substituted 5- or 6-membered nonaromaticcarbocyclic or heterocyclic ring, optionally including one or two ringmembers selected from the group consisting of C(═O), SO or S(O)₂.

[0125] Also of note are compounds for reasons of cost, ease of synthesisand/or biological efficacy:

[0126] Selection A. Compounds of Formula I illustrated as Formula Ia

[0127] wherein

[0128] A and B are independently O or S;

[0129] J is

[0130] K is taken together with the two linking atoms to form a phenylring or a 5- or 6-membered heteroaromatic ring, each ring optionallysubstituted with from 1 to 4 R⁴;

[0131] X is O or S;

[0132] R¹ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆cycloalkyl each optionally substituted with one or more substituentsselected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C₄alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino and C₃-C₆cycloalkylamino; or

[0133] R¹ is C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl;

[0134] R² is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆cycloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl;

[0135] R³ is H; G; C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆cycloalkyl, each optionally substituted with one or more substituentsselected from the group consisting of halogen, G, CN, NO₂, hydroxy,C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl,C₁-C₄ alkylsulfonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylcarbonyl, C₃-C₆trialkylsilyl, or a phenyl, phenoxy or 5- or 6-membered heteroaromaticring, each ring optionally substituted with one to three substituentsindependently selected from the group consisting of C₁-C₄ alkyl, C₂-C₄alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂,C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl,C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl,C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; C₁-C₄ alkoxy; C₁-C₄alkylamino; C₂-C₈ dialkylamino; C₃-C₆ cycloalkylamino; C₂-C₆alkoxycarbonyl or C₂-C₆ alkylcarbonyl; or

[0136] R² and R³ can be taken together with the nitrogen to which theyare attached to form a ring containing 2 to 6 atoms of carbon andoptionally one additional atom of nitrogen, sulfur or oxygen, said ringmay be optionally substituted with from 1 to 4 substituents selectedfrom the group consisting of C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂alkoxy,

[0137] G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclicring, optionally including one or two ring members selected from thegroup consisting of C(═O), SO or S(O)₂ and optionally substituted withfrom 1 to 4 substituents selected from the group consisting of C₁-C₂alkyl, halogen, CN, NO₂ and C₁-C₂ alkoxy;

[0138] each R⁴ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, hydroxy, C₁-C₄alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, or C₃-C₆ trialkylsilyl; or

[0139] each R⁴ is independently phenyl, benzyl or phenoxy, eachoptionally substituted with from one to three substituents selected fromthe group consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino,C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino,C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl,C₃-C₈ dialkylaminocarbonyl and C₃-C₆ trialkylsilyl;

[0140] each R⁵ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂,hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl,C₃-C₆ trialkylsilyl or W;

[0141] (R₅)₂ when attached to adjacent carbon atoms can be takentogether as —OCF₂O—, —CF₂CF₂O—, or —OCF₂CF₂O—;

[0142] each W is independently a phenyl, benzyl, benzoyl, phenoxy, 5- or6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-memberedfused heterobicyclic ring system, each ring optionally substituted withone to three substituents independently selected from the groupconsisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino,C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino,C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl,C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl;

[0143] m is 1 to 7; and

[0144] n is 1 to 3.

[0145] Selection B. Compounds of Selection A wherein K is taken togetherwith the two linking atoms to form a phenyl ring optionally substitutedwith from 1 to 3 R⁴.

[0146] Selection C. Compounds of Selection A wherein K is taken togetherwith the two linking atoms to form a thiophene, pyrazole, isoxazole,pyridine or pyrimidine optionally substituted with from 1 to 3 R⁴.

[0147] Selection D. Compounds of Selection B or Selection C wherein

[0148] A and B are both O;

[0149] n is 1 to 2;

[0150] R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;

[0151] R² is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;

[0152] R³ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆cycloalkyl each optionally substituted with one or more substituentsselected from the group consisting of halogen, CN, C₁-C₂ alkoxy, C₁-C₂alkylthio, C₁-C₂ alkylsulfinyl and C₁-C₂ alkylsulfonyl;

[0153] one of the R⁴ groups is attached to the K ring at one of the twopositions ortho to the two linking atoms, and said R⁴ is C₁-C₄ alkyl,C₁-C₄ haloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄haloalkylthio, C₁-C₄ haloalkylsulfinyl or C₁-C₄ haloalkylsulfonyl;

[0154] each R⁵ is independently H, C₁-C₄ alkyl, C₁-C₄ haloalkyl,halogen, CN, NO₂, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl or C₂-C₄ alkoxycarbonyl; andone R⁵ is optionally W;

[0155] W is a phenyl ring or a 5- or 6-membered heteroaromatic ring,each ring optionally substituted with from one to three substituentsindependently selected from the group consisting of C₁-C₄ alkyl, C₂-C₄alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂,C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl,C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl,C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈dialkylaminocarbonyl or C₃-C₆ trialkylsilyl.

[0156] Selection E. Compounds of Selection D wherein

[0157] J is J-1;

[0158] R¹ and R² are both H;

[0159] R³ is C₁-C₄ alkyl, C₂-C₄ alkenyl or C₂-C₄ alkynyl, eachoptionally substituted with halogen, CN, OCH₃, S(O)_(p)CH₃;

[0160] each R⁴ is independently CH₃, CF₃, OCF₃, OCHF₂, S(O)_(p)CF₃,S(O)_(p)CHF₂, CN or halogen;

[0161] each R⁵ is independently H, halogen, C₁-C₄ alkyl, CF₃, CHF₂,CH₂CF₃, S(O)_(p)CF₃, S(O)_(p)CHF₂, S(O)_(p)CH₂CF₃, S(O)_(p)CF₂CHF₂ orCN; and one R⁵ is optionally W;

[0162] W is a phenyl, pyrazole, imidazole, triazole, pyridine orpyrimidine ring, each ring optionally substituted with one to threesubstituents independently selected from the group consisting of C₁-C₄alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio,C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, halogen or CN;

[0163] m is 1 to 2; and

[0164] p is 0, 1 or 2.

[0165] Selection F. Compounds of Selection E wherein W is a phenyloptionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.

[0166] Selection G. Compounds of Selection E wherein W is a pyrazole,imidazole, triazole, pyridine or pyrimidine, each ring optionallysubstituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.

[0167] Selection H. Compounds of Selection D wherein

[0168] J is J-2;

[0169] R¹ and R² are both H;

[0170] R³ is C₁-C₄ alkyl, C₂-C₄ alkenyl or C₂-C₄ alkynyl, eachoptionally substituted with halogen, CN, OCH₃, S(O)_(p)CH₃;

[0171] each R⁴ is independently CH₃, CF₃, OCF₃, OCHF₂, S(O)_(p)CF₃,S(O)_(p)CHF₂, CN or halogen;

[0172] each R⁵ is independently H, halogen, C₁-C₄ alkyl, CF₃,S(O)_(p)CF₃, S(O)_(p)CHF₂, S(O)_(p)CH₂CF₃, S(O)_(p)CF₂CHF₂ or CN; andone R⁵ is optionally W;

[0173] W is a phenyl, pyrazole, imidazole, triazole, pyridine orpyrimidine ring, each ring optionally substituted with one to threesubstituents independently selected from the group consisting of C₁-C₄alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio,C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, halogen or CN;

[0174] m is 1 to 2; and

[0175] p is 0, 1 or 2.

[0176] The compounds of Formula I can be prepared by one or more of thefollowing methods and variations as described in Schemes 1-28. Thedefinitions of A, B, J, K, V, W, X, R¹, R², R³, R⁴, R⁵, m, n and q inthe compounds of Formulae 1-59 below are as defined above. Compounds ofFormulae Ib-Ie are various subsets of Formula I and compounds of Formula1 are also subsets of Formula I. Compounds of Formulae 1a-c, 2a-g, 9a-b,11a, 12a, 13a, 14a-c, 26a-c, 42a-c and 51a-d are various subsets of thecompounds of Formula 1, 2, 9, 11, 12, 13, 14, 26, 42 and 51respectively. In the Schemes, R¹⁰ is C₁-C₄ alkyl, unless definedotherwise.

[0177] A typical procedure is illustrated in Scheme 1 and involvescoupling of an ortho amino carboxylic acid amide of Formula 2 with anacid chloride of Formula 3 in the presence of an acid scavenger toprovide the compound of Formula Ib. Typical acid scavengers includeamine bases such as triethylamine, diisopropylethylamine and pyridine;other scavengers include hydroxides such as sodium and potassiumhydroxide and carbonates such as sodium carbonate and potassiumcarbonate. In certain instances it is useful to use polymer-supportedacid scavengers such as polymer-bound diisopropylethylamine andpolymer-bound dimethylaminopyridine. In a subsequent step, amides ofFormula Ib can be converted to thioamides of Formula Ic using a varietyof standard thio transfer reagents including phosphorus pentasulfide andLawesson's reagent.

[0178] An alternate procedure for the preparation of compounds ofFormula Ib involves coupling of an amide of Formula 2 with an acid ofFormula 4 in the presence of a dehydrative coupling agent such asdicyclohexylcarbodiimide (DCC) in Scheme 2. Polymer supported reagentssuch as polymer-bound cyclohexylcarbodiimide are useful here. Syntheticprocedures of Schemes 1 and 2 are only representative examples of usefulmethods for the preparation of Formula I compounds by coupling an aminewith an acid or acid equivalent, as the synthetic literature isextensive for this type of reaction.

[0179] One skilled in the art will also realize that acid chlorides ofFormula 3 may be prepared from acids of Formula 4 by numerous well-knownmethods.

[0180] A procedure for the preparation of compounds of Formula Idinvolves coupling of an ortho-amino carboxylic acid ester of Formula 5(wherein R¹⁰ is C₁-C₄ alkyl) with an acid chloride of Formula 3 by amethod similar to that described in Scheme 1, followed by transformationof the ester group into an amide functionality. This transformation canbe achieved by an amination with an amine of Formula 7. A Lewis acid,such as trimethylaluminum, as shown in Scheme 3 may promote thisreaction.

[0181] Alternatively the ester 6 can be transformed to an amide ofFormula Id as shown in Scheme 4 by saponification with a base such asaqueous sodium hydroxide to provide the acid of Formula 8 followed bydehydrative coupling with an amine of Formula 7 by a procedure similarto that described in Scheme 2.

[0182] Of note are compounds of Formula I wherein K is an optionallysubstituted phenyl ring. A typical procedure is detailed in Scheme 5 andinvolves coupling of an anthranilic amide of Formula 2a with an acidchloride of Formula 3 in the presence of an acid scavenger to providethe compound of Formula Ie (a subset of Formula I). Typical acidscavengers include amine bases such as triethylamine,diisopropylethylamine and pyridine; other scavengers include hydroxidessuch as sodium and potassium hydroxide and carbonates such as sodiumcarbonate and potassium carbonate. In certain instances it is useful touse polymer-supported acid scavengers such as polymer-bounddiisopropylethylamine and polymer-bound dimethylaminopyridine. In asubsequent step, amides of Formula Ie can be converted to thioamides ofFormula If (a subset of Formula I) using a variety of standard thiotransfer reagents including phosphorus pentasulfide and Lawesson'sreagent.

[0183] An alternate procedure for the preparation of compounds ofFormula Ie involves coupling of an anthranilic amide of Formula 2a withan acid of Formula 4 in the presence of a dehydrative coupling agentsuch as dicyclohexylcarbodiimide (DCC) in Scheme 6. Polymer supportedreagents such as polymer-bound cyclohexylcarbodiimide are again usefulhere. Synthetic procedures of Schemes 5 and 6 are only representativeexamples of useful methods for the preparation of Formula I compounds asthe synthetic literature is extensive for this type of reaction.

[0184] Anthranilic amides of Formula 2a are typically available from thecorresponding 2-nitrobenzamides of Formula 9 via catalytic hydrogenationof the nitro group (Scheme 7). Typical procedures involve reduction withhydrogen in the presence of a metal catalyst such as palladium on carbonor platinum oxide and in hydroxylic solvents such as ethanol andisopropanol to provide compounds of Formula 2b (Compounds of Formula 2awherein R¹ is H). These procedures are well documented in the chemicalliterature. R¹ substituents such as alkyl, substituted alkyl and thelike can generally be introduced at this stage through known proceduresincluding either direct alkylation or through the generally preferredmethod of reductive alkylation of the amine. A commonly employedprocedure is to combine the aniline 2b with an aldehyde in the presenceof a reducing agent such as sodium cyanoborohydride to produce theFormula 2c compounds (compounds of Formula 2a wherein R¹ is alkyl,alkenyl, alkynyl or substituted derivatives thereof).

[0185] The intermediate amides of Formula 9a are readily prepared fromcommercially available 2-nitrobenzoic acids of Formula 10 (Scheme 8).Typical methods for amide formation can be applied here. These includedirect dehydrative coupling of acids of Formula 10 with amines ofFormula 7 using for example DCC, and conversion of the acids to anactivated form such as the acid chlorides or anhydrides and subsequentcoupling with amines to form amides of formula 9a. Ethyl chloroformateis an especially useful reagent for this type of reaction involvingactivation of the acid. The chemical literature is extensive on thistype of reaction. Amides of Formula 9a are readily converted tothioamides of Formula 9b by using commercially available thio transferreagents such as phosphorus pentasulfide and Lawesson's reagent.

[0186] Intermediate ortho-amino carboxylic acid amides of Formulae 2dand 2e may also be prepared from anhydrides of Formulae 11 and 12respectively (Scheme 9). Typical procedures involve combination ofequimolar amounts of the amine 7 with the anhydride in polar aproticsolvents such as pyridine and dimethylformamide at temperatures rangingfrom room temperature to 100° C. R¹ substituents such as alkyl andsubstituted alkyl may be introduced by the base catalyzed alkylation ofanhydride of Formula 11 with known alkylating reagents R¹-Lg (wherein Lgis a leaving group such as halogen, alkyl or aryl suphonates or alkylsulfates) to provide the alkyl substituted intermediates of Formula 12.Anhydrides of Formula 11 may be made by methods described in Coppola,Synthesis, 1980, 505 and Fabis et al Tetrahedron, 1998, 10789.

[0187] Intermediate anththranilic amides of Formula 2f and 2 g may alsobe prepared from isatoic anhydrides of Formula 11a and 12a (Scheme 10).Typical procedures involve combination of equimolar amounts of the amine7 with the isatoic anhydride in polar aprotic solvents such as pyridineor dimethylformamide at temperatures ranging from room temperature to100° C. R¹ substituents such as alkyl and substituted alkyl may beintroduced by the base catalyzed alkylation of isatoic anhydride 11awith known alkylating reagents R¹-Lg (wherein Lg is a leaving group suchas halogen, alkyl or aryl suphonates or OSO₂OR¹) to provide the alkylsubstituted intermediates 12a.

[0188] A procedure for the preparation of compounds of Formula Ig(compounds of Formula I wherein A is O, B is O and R¹ is H) involvesreaction of an amine 7 with a heterocyclic fused oxazinone of Formula 13(Scheme 11). Typical procedures involve combination of an amine 7 with aoxazinone in solvents such as tetrahydrofuran or pyridine attemperatures ranging from room temperature to the reflux temperature ofthe solvent. Oxazinones are well documented in the chemical literatureand are available via known methods that involve the coupling of anortho amino carboxylic acid with an acid chloride. For references to thesynthesis and chemistry of heterocyclic fused oxazinones see Jakobsen etal, Biorganic and Medicinal Chemistry, 2000, 8, 2803-2812 and referencescited therein.

[0189] A procedure for the preparation of compounds of Formula Ih(compounds of Formula I wherein A is O, B is O and R¹ is H and K isoptionally substituted phenyl) involves reaction of an amine 7 with abenzoxazinone of Formula 13a (Scheme 12). Typical procedures involvecombination of the amine with the benzoxazinone in solvents such astetrahydrofuran or pyridine at temperatures ranging from roomtemperature to the reflux temperature of the solvent. Benzoxazinones arewell documented in the chemical literature and are available via knownmethods that involve the coupling of either an anthranilic acid or anisatoic anhydride with an acid chloride. For references to the synthesisand chemistry of Benzoxazinones see Jakobsen et al, Biorganic andMedicinal Chemistry, 2000, 8, 2095-2103 and references cited within. Seealso Coppola, J. Heterocyclic Chemistry, 1999, 36, 563-588.

[0190] Methods of preparation of specific J-groups (and precursorsthereof) are outlined in Schemes 13-28. In these schemes Z is any groupattached to J that can be chemically transformed to provide compounds ofFormula I. For example, Z may be CO₂H (and Z-J corresponds to Formula4), CO₂(C₁-C₄ alkyl), CN or CH₂OH. Compounds of Z-J wherein Z isCO₂(C₁-C₄ alkyl) or CN can be converted to compounds of Formula 4 byhydrolysis. The literature is extensive on the conversion of esters ornitriles to the corresponding carboxylic acids. Compounds of Z-J whereinZ is CH₂OH can be converted to compounds of Formula 4 by oxidation. Forthe conversion of these compounds into compounds of Formula 4, numerousmethods of oxidation are available and a selection may be found inComprehensive Organic Transformations, Larock, R. C., VCH Publishers,Inc, 1989. Z may also be other groups corresponding to previouslydescribed intermediates summarized in Exhibit 5.

[0191] Typical procedures for the preparation of some Z-J compounds areillustrated in Scheme 13 and involve cycloadditions of compounds ofFormulae 15 or 16 with an alkene of Formula 14 to provide compounds ofFormula 17.

[0192] Cycloadditions of compounds of Formulae 18 or 19 providecompounds of Formulae 20 and 21 respectively (Scheme 14).

[0193] The cycloadditions can be 2+4 type such as a hetero-Diels Alderreaction (see for example Waldmann, H, Synthesis, 1994, 6, 535) or canbe of the 2+3 type such as one of a number of 1,3-dipole cycloadditions(see 1,3-Dipolarcycloaddition Chemistry, Padwa, A, Ed., J. Wiley & Sons,1983).

[0194] Certain compounds of Formula 14a or 14b can be prepared bytreating compounds of Formula 2 or 2a with acrylic acids of Formula 22or acid chlorides of Formula 23 using methods analogous to thosedescribed above for Schemes 1, 2, 5 and 6 (Scheme 15). Compounds ofFormula 14c can be prepared by treating compounds of Formula 5 withcompounds of Formula 23 followed by further treatment with amines ofFormula 7 using methods analogous to those described for Schemes 3 and4.

[0195] Alternatively, some compounds of Formula Z-J can be prepared by acycloaddition of compounds of Formula 27 or Formula 28, for example,with a glyoxyl or aldehydo derivative of Formula 26 to provide compoundsof Formulae 29 and 30 respectively as shown in Scheme 16.

[0196] Alternatively, compounds of Formula 33 (a subset of Z-Jcompounds) can be prepared by a cycloaddition of an alkene of Formula 32with an oxime of Formula 31 (Scheme 17). Typically, the cycloaddition isaccomplished by treatment of the oxime of Formula 31 with a halogenatingagent such as N-chlorosuccinimide (NCS), followed by treatment with asuitable base such as triethylamine in the presence of the alkene ofFormula 32.

[0197] Certain compounds of Formula 26a or 26b can be prepared bytreating compounds of Formula 2 or 2a with glyoxylic acid of Formula 34or glyoxylic acid chloride of Formula 35 using methods analogous tothose described above for Schemes 1, 2, 5 and 6 (Scheme 18). 15Compounds of Formula 26c can be prepared by treating compounds ofFormula 5 with compounds of Formula 35 followed by further treatmentwith amines of Formula 7 using methods analogous to those described forScheme 4.

[0198] Certain compounds of Formula Z-J (Formulae 40 and 42) can also beprepared by cyclization of a hydrazide of formula 38 or thiohydrazide ofFormula 39 with a C₁ unit (Formula 26) or C₂ unit (Formula 41)respectively as illustrated in Scheme 19.

[0199] Certain compounds of Formula 42 can be prepared from compounds ofFormula 38 or 39 by treatment with epihalohydrins of Formula 43 toprovide compounds of Formula 42a (Scheme 20). Oxidation of compounds ofFormula 42a provides compounds of Formula 42b, a subset of acids ofFormula 4.

[0200] Some compounds of Formula Z-J of Formula 45 can also be preparedby reduction of an aromatic heterocycle of Formula 44 (Scheme 21).

[0201] Oximes of Formula 31 can be obtained from compounds of Formula 26by condensation with hydroxylamine under a number of conditions wellknown to those skilled in the art (Scheme 22).

[0202] Some heterocyclic acids of Formula 47 (a subset of Formula 4) canbe made via lithiation of a nonaromatic heterocycle of Formula 46 (e.g.using butyl lithium in the presence of tetramethylethylenediamine(TMEDA)) and treatment with carbon dioxide (Scheme 23).

[0203] Some heterocyclic acids of Formula 51 can be prepared by thereaction sequence illustrated in Schemes 24-25.

[0204] As illustrated in Scheme 24, a compound of Formula 48 is treatedwith a compound of Formula 49 wherein R¹⁰ is C₁-C₄ alkyl (a fumarateester or maleate ester or a mixture thereof may be used) in the presenceof a base and a solvent. The base is typically a metal alkoxide salt,such as sodium methoxide, potassium methoxide, sodium ethoxide,potassium ethoxide, potassium tert-butoxide, lithium tert-butoxide, andthe like. Greater than 0.5 equivalents of base versus the compound ofFormula 48 should be used, preferably between 0.9 and 1.3 equivalents.Greater than 1.0 equivalents of the compound of Formula 49 should beused, preferably between 1.0 to 1.3 equivalents. Polar protic and polaraprotic organic solvents can be used, such as alcohols, acetonitrile,tetrahydrofuran, N,N-dimethylformamide, dimethyl sulfoxide and the like.Preferred solvents are alcohols such as methanol and ethanol. It isespecially preferred that the alcohol be the same as that making up thefumarate or maleate ester and the alkoxide base. The reaction istypically conducted by mixing the compound of Formula 48 and the base inthe solvent. The mixture can be heated or cooled to a desiredtemperature and the compound of Formula 49 added over a period of time.Typically reaction temperatures are between 0° C. and the boiling pointof the solvent used. The reaction may be conducted under greater thanatmospheric pressure in order to increase the boiling point of thesolvent. Temperatures between about 30 and 90° C. are generallypreferred. The addition time can be as quick as heat transfer allows.Typical addition times are between 1 minute and 2 hours. Optimumreaction temperature and addition time vary depending upon theidentities of the compounds of Formula 48 and Formula 49. Afteraddition, the reaction mixture can be held for a time at the reactiontemperature. Depending upon the reaction temperature, the required holdtime may be from 0 to 2 hours. Typical hold times are 10 to 60 minutes.The reaction mass then can be acidified by adding an organic acid, suchas acetic acid and the like, or an inorganic acid, such as hydrochloricacid, sulfuric acid and the like. Depending on the reaction conditionsand the means of isolation, compounds of Formula 50 wherein R¹¹ is H orcompounds of Formula 50 wherein R¹¹ is C₁-C₄ alkyl can be prepared. Forexample, a compound of Formula 50 wherein R¹¹ is C₁-C₄ alkyl can behydrolyzed in situ to a compound of Formula 50 wherein R¹¹ is H whenwater is present in the reaction mixture. The desired product, acompound of Formula 50, can be isolated by methods known to thoseskilled in the art, such as crystallization, extraction or distillation.

[0205] In the next step, illustrated as step 1 in Scheme 25, a compoundof Formula 50 is treated with a halogenating reagent usually in thepresence of a solvent. Halogenating reagents that can be used includephosphorus oxyhalides, phosphorus trihalides, phosphorus pentahalides,thionyl chloride, dihalotrialkylphophoranes, dihalodiphenylphosphoranes,oxalyl chloride and phosgene. Preferred are phosphorus oxyhalides andphosphorus pentahalides. To obtain complete conversion, at least 0.33equivalents of phosphorus oxyhalide versus the compound of Formula 50should be used, preferably between 0.33 and 1.2 equivalents. To obtaincomplete conversion, at least 0.20 equivalents of phosphorus pentahalideversus the compound of Formula 50 should be used, preferably betweenabout 0.20 and 1.0 equivalents. Compounds of Formula 50 wherein R¹¹ isC₁-C₄ alkyl are preferred for this reaction.

[0206] Typical solvents for this halogenation include halogenatedalkanes, such as dichloromethane, chloroform, chlorobutane and the like,aromatic solvents, such as benzene, xylene, chlorobenzene and the like,ethers, such as tetrahydrofaran, p-dioxane, diethyl ether, and the like,and polar aprotic solvents such as acetonitrile, N,N-dimethylformamide,and the like. Optionally, an organic base, such as triethylamine,pyridine, N,N-dimethylaniline or the like, can be added. Addition of acatalyst, such as N,N-dimethylformamide, is also an option. Preferred isthe process in which the solvent is acetonitrile and a base is absent.Typically, neither a base nor a catalyst is required when acetonitrilesolvent is used. The preferred process is conducted by mixing thecompound of Formula 50 in acetonitrile. The halogenating reagent is thenadded over a convenient time and the mixture is then held at the desiredtemperature until the reaction is complete. The reaction temperature istypically between 20° C. and the boiling point of acetonitrile, and thereaction time is typically less than 2 hours. The reaction mass is thenneutralized with an inorganic base, such as sodium bicarbonate, sodiumhydroxide and the like, or an organic base, such as sodium acetate. Thedesired product, a compound of Formula 51, can be isolated by methodsknown to those skilled in the art, including crystallization, extractionand distillation.

[0207] The halogen in compounds of Formula 51a may be displaced by anucleophile (Nuc) such as the sodium or potassium salt of C₁-C₄ alkoxy,C₁-C₄ haloalkoxy, C₁-C₄ alkylthio or C₁-C₄ haloalkylthio (step 3 inScheme 25). These displacements can be carried out in solvents such asethers, such as tetrahydrofuran, p-dioxane, diethyl ether, and the like,and polar aprotic solvents such as acetonitrile, N,N-dimethylformamide,and the like. The reaction temperature is typically between 20° C. andthe boiling point of the solvent.

[0208] The compounds of Formula 51a or Formula 51c wherein R¹¹ is C₁-C₄alkyl, an ester, can be hydrolyzed to compounds of Formula 51b orFormula 51d, respectively, wherein R¹¹ is H, a carboxylic acid (step 2or step 4 of Scheme 25). These hydrolyses can be catalyzed by acids,metal ions, and by enzymes. Iodotrimethylsilane is noted as an exampleof an acid which can be used to catalyze these hydrolyses (see AdvancedOrganic Chemistry, Third Ed., Jerry March, John Wiley & Sons, Inc. NewYork, 1985, pp. 334-338 for a review of methods). Base-catalyzedhydrolytic methods are not recommended for the hydrolysis of compoundsof Formula 51 and can result in decomposition. The carboxylic acids canbe isolated by methods known to those skilled in the art, includingcrystallization, extraction and distillation.

[0209] Some heterocyclic acids of Formula 55 can be prepared by thereaction sequence illustrated in Schemes 26-28.

[0210] As illustrated in Scheme 26, compounds of Formula 53 can beprepared from compounds of Formula 52 by treatment with a suitable basein a suitable organic solvent. Examples of suitable bases include (butare not limited to) sodium hydride, potassium t-butoxide, dimsyl sodium(CH₃SOCH₂ ⁻Na⁺), alkali metal (such as lithium, sodium or potassium)carbonates or hydroxides, tetraalkyl (such as methyl, ethyl orbutyl)ammonium fluorides or hydroxides, or2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphonine.Examples of suitable organic solvents include (but are not limited to)acetone, acetonitrile, tetrahydrofuran, dichloromethane,dimethylsulfoxide, or N,N-dimethylformamide. The cyclization reaction isusually conducted in a temperature range from about 0 to 120° C. Theeffects of solvent, base, temperature and addition time are allinterdependent, and choice of reaction conditions is important tominimize the formation of byproducts. A preferred base istetrabutylammonium fluoride. The intermediate formed in the reaction,Formula 53 wherein M⁺ is a suitable counterion derived from the base, isthen protonated by a suitable acid (for example, acetic acid) to givecompounds of Formula 54a wherein R¹² is H. As one skilled in the artwill know, intermediates such as 53 may be alkylated by the addition ofa suitable alkylating agent to give compounds of Formula 54b wherein R¹²is C₁-C₄ alkyl. Alternatively, compounds of Formula 54b can be preparedfrom compounds of Formula 54a in a separate chemical step using asuitable base and alkylating agent. Suitable alkylating agents includeC₁-C₄ alkyl halides (e.g. ethyl iodide), sulfates (e.g. dimethylsulfate)and sulfonates (e.g. methyl p-toluenesulfonate).

[0211] Cleavage of a compound of Formula 54b can provide a compound of55. This conversion can be catalyzed by bases, nucleophiles, metal ions,and by enzymes. Some cleavage methods include treatment with lithiumchloride or lithium iodide in solvents such as N,N-dimethylformamide orpyridine, treatment with magnesium iodide in toluene, and treatment withpotassium-t-butoxide in dimethylsulfoxide or water. Methods of estercleavage are reviewed in Greene, T. W.; Wuts, P. G. M. Protective Groupsin Organic Synthesis, 2nd ed.; Wiley: New York, 1991. Acid-catalyzedhydrolytic methods are not recommended for the hydrolysis of compoundsof Formula 54b and can result in decomposition. The carboxylic acid canbe isolated by methods known to those skilled in the art, includingcrystallization, extraction and distillation.

[0212] Compounds of Formula 52 can be prepared by treatment of compoundsof Formula 56 with compounds of Formula 57 in a suitable organic solventin the presence of an acid scavenger such as triethylamine. Examples ofsuitable organic solvents include (but are not limited to)dichioromethane and tetrahydrofuran. The reaction is usually conductedat a temperature between about 0 and 100° C. Scheme 27 illustrates thistransformation.

[0213] As illustrated by Scheme 28, the hydrazone compound of Formula 56can be prepared from hydrazine compound of Formula 58 by treatment witha compound of Formula 59 in a solvent such as water, methanol or aceticacid. One skilled in the art will recognize that this reaction mayrequire catalysis by an optional acid and may also require elevatedtemperatures depending on the molecular substitution pattern of thehydrazone of Formula 56.

[0214] It is recognized that some reagents and reaction conditionsdescribed above for preparing compounds of Formula I may not becompatible with certain functionalities present in the intermediates. Inthese instances, the incorporation of protection/deprotection sequencesor functional group interconversions into the synthesis will aid inobtaining the desired products. The use and choice of the protectinggroups will be apparent to one skilled in chemical synthesis (see, forexample, Greene, T. W.; Wuts, P. G. M. Protective Groups in OrganicSynthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art willrecognize that, in some cases, after the introduction of a given reagentas it is depicted in any individual scheme, it may be necessary toperform additional routine synthetic steps not described in detail tocomplete the synthesis of compounds of Formula L. One skilled in the artwill also recognize that it may be necessary to perform a combination ofthe steps illustrated in the above schemes in an order other than thatimplied by the particular sequence presented to prepare the compounds ofFormula 1.

[0215] One skilled in the art will also recognize that compounds ofFormula I and the intermediates described herein can be subjected tovarious electrophilic, nucleophilic, radical, organometallic, oxidation,and reduction reactions to add substituents or modify existingsubstituents.

[0216] Without further elaboration, it is believed that one skilled inthe art using the preceding description can utilize the presentinvention to its fullest extent. The following Examples are, therefore,to be construed as merely illustrative, and not limiting of thedisclosure in any way whatsoever. Percentages are by weight except forchromatographic solvent mixtures or where otherwise indicated. Parts andpercentages for chromatographic solvent mixtures are by volume unlessotherwise indicated. ¹H NMR spectra are reported in ppm downfield fromtetramethylsilane; s is singlet, d is doublet, t is triplet, q isquartet, m is multiplet, dd is doublet of doublets, dt is doublet oftriplets, br s is broad singlet.

EXAMPLE 1 Preparation of1-(2-Chlorophenyl)-4,5-dihydro-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-trifluoromethyl)-1H-pyrazole-5-carboxamide

[0217] Step A: Preparation of 3-methyl-N-(1-methylethyl-2-nitrobenzamide

[0218] A solution of 3-methyl-2-nitrobenzoic acid (2.00 g, 11.0 mmol)and triethylamine (1.22 g, 12.1 mmol) in 25 mL of dichloromethane wascooled to 10° C. Ethyl chloroformate was carefully added and a solidprecipitate formed. After the reaction mixture was stirred for 30minutes, isopropylamine (0.94 g, 16.0 mmol) was added and a homogeneoussolution resulted. The reaction mixture was stirred for an additionalhour, poured into water and extracted with ethyl acetate. The organicextracts were washed with water, dried over magnesium sulfate andevaporated under reduced pressure to afford 1.96 g of the title compoundas a white solid melting at 126-128° C.

[0219]¹H NMR (CDCl₃) δ 1.24 (d, 6H), 2.38 (s, 3H), 4.22 (m, 1H), 5.80(br s, 1H), 7.4 (m,3H).

[0220] Step B: Preparation of2-amino-3-methyl-N-(1-methylethyl)benzamide

[0221] The 2-nitrobenzamide of Step A (1.70 g, 7.6 mmol) washydrogenated over 5% Pd on carbon in 40 mL of ethanol at 345 kPa (50psi). When the uptake of hydrogen ceased the reaction was filteredthrough Celite® and the Celite® was washed with ether. The filtrate wasevaporated under reduced pressure to afford 1.41 g of the title compoundas a solid melting at 149-151° C.

[0222]¹H NMR (CDCl₃) δ 1.24 (dd, 6H), 2.16 (s, 3H), 4.25 (m, 1H), 5.54(br s, 2H), 5.85 (br s, 1H), 6.59 (t, 1H), 7.13 (d, 1H), 7.17 (d, 1H).

[0223] Step) C: Preparation of3-Methyl-N-(1-methylethyl)-2-[(1-oxo-2-propenyl)amino]benzamide

[0224] To a solution of the title compound of Step B (0.93 g, 4.8 mmol)in dichloromethane (10 mL) was added triethylamine (0.876 mL, 6.2 mmol)and the mixture was cooled to 0° C. Acryloyl chloride (0.433 mL, 5.3mmol) was then added and the mixture was warmed to ambient temperatureand stirred overnight. Dimethylaminopyridine (1.0 g, 7.7 mmol) was thenadded followed by acryloyl chloride (0.475 mL, 5.8 mmol). The mixturewas stirred at ambient temperature for 0.5 h before being diluted with1N HCl and extracted twice with dichloromethane. The organic extractswere dried (MgSO₄) and concentrated to give the product of Step C (0.62g) as a white solid.

[0225]¹H NMR (CDCl₃) δ: 9.1 (bs, 1H); 7.4-7.1 (m, 3H), 6.5-6.3 (m, 2H),6.1-6.0 (bd, 1H), 5.8-5.7 (m, 1H), 4.3-4.1 (m, 1H), 2.25 (s, 3H), 1.20(d, 6H).

[0226] Step D: Preparation ofN-(2-chlorophenyl)-2,2,2-trifluoroethanehydrazonic acid

[0227] To a solution of 2-chlorophenylhydrazine (1.65 g, 11.6 mmol) intetrahydrofuran (40 mL) at 0° C. was added trifluoroacetic anhydride(1.8 mL, 12.8 mmol). The mixture was allowed to warm gradually toambient temperature and stirred overnight. The mixture was concentrated,re-dissolved in ethyl ether and twice washed with a saturated solutionof NaHCO₃. The mixture was dried (MgSO4) and concentrated to give thetitle compound of Step D as a pale orange solid (2.77 g).

[0228]¹H NMR (CDCl₃) δ: 7.32 (dd, 1H); 7.20 (s, 1H), 6.91 (td, 1H), 6.86(dd, 1H), 6.49 (s, 1H).

[0229] Step E: Preparation of 4-Methylbenzenesulfonic acid anhydridewith N-(2-chlorophenyl)-2,2,2-trifluoroethanehydrazonic acid

[0230] To a solution of the title compound of Step D (2.77 g, 11.6 mmol)in ethyl acetate (20 mL) was added 4-Methyl morpholine (1.4 mL, 12.8mmol) followed by p-toluenesulfonyl chloride (2.43 g, 12.8 mmol). Themixture was stirred overnight at ambient temperature and then dilutedwith ethyl ether, twice washed with 1N HCl, was dried (MgSO₄) andconcentrated. The residue was triturated with hexane to yield the titlecompound of step E as a white solid.

[0231]¹H NMR (CDCl₃) δ: 9.0-8.9 (bs, 1H), 8.0-7.9 (d, 2H), 7.6-7.5 (d,1H); 7.5-7.4 (d, 2H), 7.4-7.2 (m, 2H), 7.0-6.9 (t, 1H), 2.50 (s, 3H).

[0232] Step F: Preparation of1-(2-Chlorophenyl)-4,5-dihydro-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-trifluoromethyl)-1H-pyrazole-5-carboxamide

[0233] To a solution of the title compound of Step C (0.24 g, 0.98 mmol)in ethyl acetate (15 mL) was added 4-methyhmorpholine (0.267 mL, 2.45mmol) and the compound of Step E (0.421 g, 1.08 mmol) and the mixturewas heated at reflux for 24 hours. The mixture was cooled, diluted withdichloromethane, washed with water, dried (MgSO₄) and concentrated. Theresidue was purified by flash column chromatography (5% then 10% then20% ethyl acetate in toluene) to give the title compound of Example 1, acompound of the invention, as a white solid (21 mg).

[0234]¹H NMR (CDCl₃) δ: 9.4 (bs, 1H), 7.6-7.5 (d, 1H), 7.4-7.1 (m, 6H),5.8 (bd, 1H), 5.4 (dd, 1H), 4.3-4.1 (m, 1H), 3.6-3.4 (m, 2H), 1.84 (s,3H), 1.3-1.2 (m, 6H).

EXAMPLE 2 Preparation of Methyl1-(2-chlorophenyl)-4,5-dihydro-5-[[[2-methyl-6-[[(1-methylethylamino]carbonyl]phenyl]amino]carbonyl]1H-pyrazole-3-carboxylate

[0235] Step A: Preparation of Methyl(2E)-[(2-chlorophenyl)hydrazono]acetate

[0236] To a solution of methyl glyoxylate (6.8 g, 77 mmol) in methanol(150 mL) was added 2-chlorophenylhydrazine hydrochloride (12.5 g, 77mmol) and the mixture was heated at reflux overnight, cooled andconcentrated. The residue was re-dissolved in toluene and concentratedto give the title compound of Step A.

[0237]¹H NMR (CDCl₃) δ: 12.6 (bs, 1H), 7.7-7.6 (d, 1H), 7.4-7.3 (d, 1H),7.3-7.2 (m, 1H), 7.0-6.9 (m, 1H), 6.77 (s, 1H), 3.84 (s, 3H).

[0238] Step B: Preparation of Methyl(2Z)-bromo[(2-chlorophenyl)hydrazono]acetate

[0239] To a solution of the title compound of Step A (16.5 g, 77 mmol)in tetrahydrofuran (150 mL) was added N-bromosuccinimide (13.7 g, 77mmol) and the mixture was stirred at ambient temperature for 2 hours.The mixture was concentrated and extracted with hexane and the hexanesolution was concentrated to give the title compound of Step B (16 g) asan orange solid.

[0240]¹H NMR (CDCl₃) δ: 8.93 (bs, 1H), 7.63 (dd, 1H), 7.34 (dd, 1H),7.28 (m, 1H), 6.98 (m, 1H), 3.95 (s, 3H).

[0241] Step C: Preparation of Methyl1-(2-chlorophenyl)-4,5-dihydro-5-[[[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]amino]carbonyl]1H-pyrazole-3-carboxylate

[0242] To a solution of the product of Example 1, Step C (1.0 g, 4.1mmol) and the product of Example 2, Step B (2.4 g, 8.2 mmol) in ethylacetate (50 mL) was added 4-methyl-morpholine (1.1 mL, 12.3 mmol) andthe mixture was heated at reflux for 2 hours. A further amount of4-methylmorpholine was added (1.1 mL, 12.3 mmol) followed by the productof Step B (2.4 g, 8.2 mmol) and the reaction mixture was heated atreflux overnight. The mixture was stirred at ambient temperature for 2days before being diluted with ethyl acetate, washed with 1N HCl, dried(MgSO₄) and concentrated. The residue was purified by flash columnchromatography (10% then 20% then 30% ethyl acetate in toluene) to givecompound the title compound of Example 2, a compound of the invention(22 mg) as an off white solid.

[0243]¹H NMR (CDCl₃) δ: 9.4-9.3 (bs, 1H), 7.6 (d, 1H), 7.4-7.3 (d, 1H),7.3-7.0 (m 5H), 5.8 (d, 1H), 5.5 (dd, 1H), 4.2-4.1 (m, 1H), 3.89 (s,3H), 3.7-3.4 (m, 2H), 1.81 (s, 3H), 1.3-1.2 (m, 6H).

EXAMPLE 3 Preparation of4-(2-Chlorophenyl)-5,6-dihydro-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-2-(trifluoromethyl)-4H-1,3,4-oxadiazine-5-carboxamide

[0244] Step A: Preparation of4-(2-Chlorophenyl)-5,6-dihydro-2-(trifluoromethyl-4H-1,3,4-oxadiazine-5-methanol

[0245] To a solution of the title compound of Example 1, step D (9.0 g,37.7 mmol) in N,N-dimethylformamide (100 mL) was added potassiumcarbonate (7.8 g, 56.6 mmol) and epibromohydrin (5.6 mL, 45.3 mmol) andthe mixture was heated at 90° C. for 1 hour. The mixture was thencooled, diluted with ethyl ether and twice washed with water. Thesolution was dried (MgSO₄), concentrated and purified by flash columnchromatography (silica gel, 20% ethyl ether in petroleum ether) to givethe title compound of step A contaminated with an equimolar amount ofthe regioisomer (2.4 g) as an orange oil.

[0246]¹H NMR (CDCl₃) δ 6 7.5-7.2 (m, 3H), 7.2-7.1 (m, 1H), 4.72 (dd,1H), 4.60 (dd, 1H), 4.2-3.7 (2xm, 2H), 3.7 (m, 1H).

[0247] Step B: Preparation of4-(2-Chlorophenyl)-5,6-dihydro-2-(trifluoromethyl)-4H-1,3,4-oxadiazine-5-carboxylicacid

[0248] To a solution of the title compound of Step A (2.1 g, 7.1 mmol)in dichloromethane (30 mL) was added dried, powdered 4 Å molecularsieves (9 g) and pyridinium chlorochromate (1.54 g, 7.1 mmol) and themixture was stirred at ambient temperature overnight. The mixture wasthen filtered through a pad of silica gel, washing with ethyl ether andconcentrated. The residue was purified by flash column chromatography(silica gel, 20% then 40% ethyl ether in petroleum ether) to give 1.1 gof a colorless oil. This material was then dissolved in t-Butanol (35mL) and water (35 mL). A solution of 2-methyl-2-butene (1.0M intetrahydrofuran, 35 mL), sodium dihydrogen phosphate (3.16 g, 26.4 mmol)and sodium chlorate (2.9 g, 32.0 mmol) were then added and the mixturewas stirred at ambient temperature overnight. The mixture was twiceextracted with dichloromethane, dried (MgSO₄), concentrated and purifiedby flash column chromatography (silica gel, 40% ethyl ether in petroleumether then ethyl ether then 10% methanol in dichloromethane) to give thetitle compound of step B (58 mg) as a colorless oil.

[0249]¹H NMR (CDCl₃) δ 7.6-7.5 (d, 1H), 7.4-7.2 (m, 2H), 7.1 (t, 1H),5.6-5.0 (bs, 1H), 4.9 (s, 1H), 4.8 (d, 1H), 4.6 (m, 1H).

[0250] Step C: Preparation of4-(2-Chlorophenyl)-5,6-dihydro-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-2-(trifluoromethyl)₄H-1,3,4-oxadiazine-5-carboxamide

[0251] To a solution of the title compound of Step B (58 mg, 0.19 mmol)in dichloromethane (10 mL) was added 2 drops of N,N-dimethylformamidefollowed by oxalyl chloride (20 μL, 0.23 mmol) and the mixture wasstirred at ambient temperature for 45 minutes. The mixture was thenconcentrated and redissolved in dichloromethane (10 mL). The titlecompound of Example 1, Step B was then added (36 mg, 0.19 mmol) followedby N,N-dimethylamino-pyridine (2 mg, 0.02 mmol) and triethylamine (40μL, 0.29 mmol) and the mixture was stirred at ambient temperatureovernight. A saturated solution of sodium bicarbonate was then added andthe mixture was filtered through a Celite® cartridge, concentrated andpurified by flash column chromatography (silica gel, 20% then 40% the60% ethyl ether in petroleum ether) to give the title compound ofExample 3 (8 mg) as a white solid.

[0252]¹H NMR (CDCl₃) δ: 9.6 (s, 1H), 7.6-7.1 (m, 7H), 5.9-5.8 (d, 1H),5.0-4.9 (dd, 1H), 4.8-4.7 (m, 1H), 4.3 (dd, 1H), 4.2-4.1 (m, 1H), 2.10(s, 3H), 1.3-1.2 (m, 6H).

[0253] By the procedures described herein together with methods known inthe art, the following compounds of Tables 1 to 13 can be prepared. Thefollowing abbreviations are used in the Tables: t means tertiary, smeans secondary, i means iso, Me means methyl, Et means ethyl, Pr meanspropyl, i-Pr means isopropyl, t-Bu means tert butyl. TABLE 1

R⁶(a) R⁵(a) R⁴(a) R⁴(b) R³ R² R⁶(a) R⁵(a) R⁴(a) R⁴(b) R³ R² Cl CF₃ CH₃ HMe H Cl CF₃ Cl H Me H Cl CF₃ CH₃ H Et H Cl CF₃ Cl H Et H Cl CF₃ CH₃ Hi-Pr H Cl CF₃ Cl H i-Pr H Cl CF₃ CH₃ H t-Bu H Cl CF₃ Cl H t-Bu H Cl CF₃CH₃ H Me Me Cl CF₃ Cl H Me Me Br CF₃ CH₃ H Me H Br CF₃ Cl H Me H Br CF₃CH₃ H Et H Br CF₃ Cl H Et H Br CF₃ CH₃ H i-Pr H Br CF₃ Cl H i-Pr H BrCF₃ CH₃ H t-Bu H Br CF₃ Cl H t-Bu H Br CF₃ CH₃ H Me Me Br CF₃ Cl H Me MeCl Cl CH₃ H Me H Cl Cl Cl H Me H Cl Cl CH₃ H Et H Cl Cl Cl H Et H Cl ClCH₃ H i-Pr H Cl Cl Cl H i-Pr H Cl Cl CH₃ H t-Bu H Cl Cl Cl H t-Bu H ClCl CH₃ H Me Me Cl Cl Cl H Me Me Br Cl CH₃ H Me H Br Cl Cl H Me H Br ClCH₃ H Et H Br Cl Cl H Et H Br Cl CH₃ H i-Pr H Br Cl Cl H i-Pr H Br ClCH₃ H t-Bu H Br Cl Cl H t-Bu H Br Cl CH₃ H Me Me Br Cl Cl H Me Me Cl BrCH₃ H Me H Cl Br Cl H Me H Cl Br CH₃ H Et H Cl Br Cl H Et H Cl Br CH₃ Hi-Pr H Cl Br Cl H i-Pr H Cl Br CH₃ H t-Bu H Cl Br Cl H t-Bu H Cl Br CH₃H Me Me Cl Br Cl H Me Me Br Br CH₃ H Me H Br Br Cl H Me H Br Br CH₃ H EtH Br Br Cl H Et H Br Br CH₃ H i-Pr H Br Br Cl H i-Pr H Br Br CH₃ H t-BuH Br Br Cl H t-Bu H Br Br CH₃ H Me Me Br Br Cl H Me Me Cl OCH₂CF₃ CH₃ HMe H Cl OCH₂CF₃ Cl H Me H Cl OCH₂CF₃ CH₃ H Et H Cl OCH₂CF₃ Cl H Et H ClOCH₂CF₃ CH₃ H i-Pr H Cl OCH₂CF₃ Cl H i-Pr H Cl OCH₂CF₃ CH₃ H t-Bu H ClOCH₂CF₃ Cl H t-Bu H Cl OCH₂CF₃ CH₃ H Me Me Cl OCH₂CF₃ Cl H Me Me BrOCH₂CF₃ CH₃ H Me H Br OCH₂CF₃ Cl H Me H Br OCH₂CF₃ CH₃ H Et H Br OCH₂CF₃Cl H Et H Br OCH₂CF₃ CH₃ H i-Pr H Br OCH₂CF₃ Cl H i-Pr H Br OCH₂CF₃ CH₃H t-Bu H Br OCH₂CF₃ Cl H t-Bu H Br OCH₂CF₃ CH₃ H Me Me Br OCH₂CF₃ Cl HMe Me Cl CF₃ CH₃ F Me H Cl CF₃ Cl F Me H Cl CF₃ CH₃ F Et H Cl CF₃ Cl FEt H Cl CF₃ CH₃ F i-Pr H Cl CF₃ Cl F i-Pr H Cl CF₃ CH₃ F t-Bu H Cl CF₃Cl F t-Bu H Cl CF₃ CH₃ F Me Me Cl CF₃ Cl F Me Me Br CF₃ CH₃ F Me H BrCF₃ Cl F Me H Br CF₃ CH₃ F Et H Br CF₃ Cl F Et H Br CF₃ CH₃ F i-Pr H BrCF₃ Cl F i-Pr H Br CF₃ CH₃ F t-Bu H Br CF₃ Cl F t-Bu H Br CF₃ CH₃ F MeMe Br CF₃ Cl F Me Me Cl Cl CH₃ F Me H Cl Cl Cl F Me H Cl Cl CH₃ F Et HCl Cl Cl F Et H Cl Cl CH₃ F i-Pr H Cl Cl Cl F i-Pr H Cl Cl CH₃ F t-Bu HCl Cl Cl F t-Bu H Cl Cl CH₃ F Me Me Cl Cl Cl F Me Me Br Cl CH₃ F Me H BrCl Cl F Me H Br Cl CH₃ F Et H Br Cl Cl F Et H Br Cl CH₃ F i-Pr H Br ClCl F i-Pr H Br Cl CH₃ F t-Bu H Br Cl Cl F t-Bu H Br Cl CH₃ F Me Me Br ClCl F Me Me Cl Br CH₃ F Me H Cl Br Cl F Me H Cl Br CH₃ F Et H Cl Br Cl FEt H Cl Br CH₃ F i-Pr H Cl Br Cl F i-Pr H Cl Br CH₃ F t-Bu H Cl Br Cl Ft-Bu H Cl Br CH₃ F Me Me Cl Br Cl F Me Me Br Br CH₃ F Me H Br Br Cl F MeH Br Br CH₃ F Et H Br Br Cl F Et H Br Br CH₃ F i-Pr H Br Br Cl F i-Pr HBr Br CH₃ F t-Bu H Br Br Cl F t-Bu H Br Br CH₃ F Me Me Br Br Cl F Me MeCl OCH₂CF₃ CH₃ F Me H Cl OCH₂CF₃ Cl F Me H Cl OCH₂CF₃ CH₃ F Et H ClOCH₂CF₃ Cl F Et H Cl OCH₂CF₃ CH₃ F i-Pr H Cl OCH₂CF₃ Cl F i-Pr H ClOCH₂CF₃ CH₃ F t-Bu H Cl OCH₂CF₃ Cl F t-Bu H Cl OCH₂CF₃ CH₃ F Me Me ClOCH₂CF₃ Cl F Me Me Br OCH₂CF₃ CH₃ F Me H Br OCH₂CF₃ Cl F Me H Br OCH₂CF₃CH₃ F Et H Br OCH₂CF₃ Cl F Et H Br OCH₂CF₃ CH₃ F i-Pr H Br OCH₂CF₃ Cl Fi-Pr H Br OCH₂CF₃ CH₃ F t-Bu H Br OCH₂CF₃ Cl F t-Bu H Br OCH₂CF₃ CH₃ FMe Me Br OCH₂CF₃ Cl F Me Me Cl CF₃ CH₃ Cl Me H Cl CF₃ Cl Cl Me H Cl CF₃CH₃ Cl Et H Cl CF₃ Cl Cl Et H Cl CF₃ CH₃ Cl i-Pr H Cl CF₃ Cl Cl i-Pr HCl CF₃ CH₃ Cl t-Bu H Cl CF₃ Cl Cl t-Bu H Cl CF₃ CH₃ Cl Me Me Cl CF₃ ClCl Me Me Br CF₃ CH₃ Cl Me H Br CF₃ Cl Cl Me H Br CF₃ CH₃ Cl Et H Br CF₃Cl Cl Et H Br CF₃ CH₃ Cl i-Pr H Br CF₃ Cl Cl i-Pr H Br CF₃ CH₃ Cl t-Bu HBr CF₃ Cl Cl t-Bu H Br CF₃ CH₃ Cl Me Me Br CF₃ Cl Cl Me Me Cl Cl CH₃ ClMe H Cl Cl Cl Cl Me H Cl Cl CH₃ Cl Et H Cl Cl Cl Cl Et H Cl Cl CH₃ Cli-Pr H Cl Cl Cl Cl i-Pr H Cl Cl CH₃ Cl t-Bu H Cl Cl Cl Cl t-Bu H Cl ClCH₃ Cl Me Me Cl Cl Cl Cl Me Me Br Cl CH₃ Cl Me H Br Cl Cl Cl Me H Br ClCH₃ Cl Et H Br Cl Cl Cl Et H Br Cl CH₃ Cl i-Pr H Br Cl Cl Cl i-Pr H BrCl CH₃ Cl t-Bu H Br Cl Cl Cl t-Bu H Br Cl CH₃ Cl Me Me Br Cl Cl Cl Me MeCl Br CH₃ Cl Me H Cl Br Cl Cl Me H Cl Br CH₃ Cl Et H Cl Br Cl Cl Et H ClBr CH₃ Cl i-Pr H Cl Br Cl Cl i-Pr H Cl Br CH₃ Cl t-Bu H Cl Br Cl Cl t-BuH Cl Br CH₃ Cl Me Me Cl Br Cl Cl Me Me Br Br CH₃ Cl Me H Br Br Cl Cl MeH Br Br CH₃ Cl Et H Br Br Cl Cl Et H Br Br CH₃ Cl i-Pr H Br Br Cl Cli-Pr H Br Br CH₃ Cl t-Bu H Br Br Cl Cl t-Bu H Br Br CH₃ Cl Me Me Br BrCl Cl Me Me Cl OCH₂CF₃ CH₃ Cl Me H Cl OCH₂CF₃ Cl Cl Me H Cl OCH₂CF₃ CH₃Cl Et H Cl OCH₂CF₃ Cl Cl Et H Cl OCH₂CF₃ CH₃ Cl i-Pr H Cl OCH₂CF₃ Cl Cli-Pr H Cl OCH₂CF₃ CH₃ Cl t-Bu H Cl OCH₂CF₃ Cl Cl t-Bu H Cl OCH₂CF₃ CH₃Cl Me Me Cl OCH₂CF₃ Cl Cl Me Me Br OCH₂CF₃ CH₃ Cl Me H Br OCH₂CF₃ Cl ClMe H Br OCH₂CF₃ CH₃ Cl Et H Br OCH₂CF₃ Cl Cl Et H Br OCH₂CF₃ CH₃ Cl i-PrH Br OCH₂CF₃ Cl Cl i-Pr H Br OCH₂CF₃ CH₃ Cl t-Bu H Br OCH₂CF₃ Cl Cl t-BuH Br OCH₂CF₃ CH₃ Cl Me Me Br OCH₂CF₃ Cl Cl Me Me Cl CF₃ CH₃ Br Me H ClCF₃ Cl Br Me H Cl CF₃ CH₃ Br Et H Cl CF₃ Cl Br Et H Cl CF₃ CH₃ Br i-Pr HCl CF₃ Cl Br i-Pr H Cl CF₃ CH₃ Br t-Bu H Cl CF₃ Cl Br t-Bu H Cl CF₃ CH₃Br Me Me Cl CF₃ Cl Br Me Me Br CF₃ CH₃ Br Me H Br CF₃ Cl Br Me H Br CF₃CH₃ Br Et H Br CF₃ Cl Br Et H Br CF₃ CH₃ Br i-Pr H Br CF₃ Cl Br i-Pr HBr CF₃ CH₃ Br t-Bu H Br CF₃ Cl Br t-Bu H Br CF₃ CH₃ Br Me Me Br CF₃ ClBr Me Me Cl Cl CH₃ Br Me H Cl Cl Cl Br Me H Cl Cl CH₃ Br Et H Cl Cl ClBr Et H Cl Cl CH₃ Br i-Pr H Cl Cl Cl Br i-Pr H Cl Cl CH₃ Br t-Bu H Cl ClCl Br t-Bu H Cl Cl CH₃ Br Me Me Cl Cl Cl Br Me Me Br Cl CH₃ Br Me H BrCl Cl Br Me H Br Cl CH₃ Br Et H Br Cl Cl Br Et H Br Cl CH₃ Br i-Pr H BrCl Cl Br i-Pr H Br Cl CH₃ Br t-Bu H Br Cl Cl Br t-Bu H Br Cl CH₃ Br MeMe Br Cl Cl Br Me Me Cl Br CH₃ Br Me H Cl Br Cl Br Me H Cl Br CH₃ Br EtH Cl Br Cl Br Et H Cl Br CH₃ Br i-Pr H Cl Br Cl Br i-Pr H Cl Br CH₃ Brt-Bu H Cl Br Cl Br t-Bu H Cl Br CH₃ Br Me Me Cl Br Cl Br Me Me Br Br CH₃Br Me H Br Br Cl Br Me H Br Br CH₃ Br Et H Br Br Cl Br Et H Br Br CH₃ Bri-Pr H Br Br Cl Br i-Pr H Br Br CH₃ Br t-Bu H Br Br Cl Br t-Bu H Br BrCH₃ Br Me Me Br Br Cl Br Me Me Cl OCH₂CF₃ CH₃ Br Me H Cl OCH₂CF₃ Cl BrMe H Cl OCH₂CF₃ CH₃ Br Et H Cl OCH₂CF₃ Cl Br Et H Cl OCH₂CF₃ CH₃ Br i-PrH Cl OCH₂CF₃ Cl Br i-Pr H Cl OCH₂CF₃ CH₃ Br t-Bu H Cl OCH₂CF₃ Cl Br t-BuH Cl OCH₂CF₃ CH₃ Br Me Me Cl OCH₂CF₃ Cl Br Me Me Br OCH₂CF₃ CH₃ Br Me HBr OCH₂CF₃ Cl Br Me H Br OCH₂CF₃ CH₃ Br Et H Br OCH₂CF₃ Cl Br Et H BrOCH₂CF₃ CH₃ Br i-Pr H Br OCH₂CF₃ Cl Br i-Pr H Br OCH₂CF₃ CH₃ Br t-Bu HBr OCH₂CF₃ Cl Br t-Bu H Br OCH₂CF₃ CH₃ Br Me Me Br OCH₂CF₃ Cl Br Me MeCl CF₃ CH₃ I Me H Cl CF₃ Cl I Me H Cl CF₃ CH₃ I Et H Cl CF₃ Cl I Et H ClCF₃ CH₃ I i-Pr H Cl CF₃ Cl I i-Pr H Cl CF₃ CH₃ I t-Bu H Cl CF₃ Cl I t-BuH Cl CF₃ CH₃ I Me Me Cl CF₃ Cl I Me Me Br CF₃ CH₃ I Me H Br CF₃ Cl I MeH Br CF₃ CH₃ I Et H Br CF₃ Cl I Et H Br CF₃ CH₃ 1 i-Pr H Br CF₃ Cl Ii-Pr H Br CF₃ CH₃ I t-Bu H Br CF₃ Cl I t-Bu H Br CF₃ CH₃ I Me Me Br CF₃Cl I Me Me Cl Cl CH₃ I Me H Cl Cl Cl I Me H Cl Cl CH₃ I Et H Cl Cl Cl IEt H Cl Cl CH₃ I i-Pr H Cl Cl Cl I i-Pr H Cl Cl CH₃ I t-Bu H Cl Cl Cl It-Bu H Cl Cl CH₃ I Me Me Cl Cl Cl I Me Me Br Cl CH₃ I Me H Br Cl Cl I MeH Br Cl CH₃ I Et H Br Cl Cl I Et H Br Cl CH₃ I i-Pr H Br Cl Cl I i-Pr HBr Cl CH₃ I t-Bu H Br Cl Cl I t-Bu H Br Cl CH₃ I Me Me Br Cl Cl I Me MeCl Br CH₃ I Me H Cl Br Cl I Me H Cl Br CH₃ I Et H Cl Br Cl I Et H Cl BrCH₃ I i-Pr H Cl Br Cl I i-Pr H Cl Br CH₃ I t-Bu H Cl Br Cl I t-Bu H ClBr CH₃ I Me Me Cl Br Cl I Me Me Br Br CH₃ I Me H Br Br Cl I Me H Br BrCH₃ I Et H Br Br Cl I Et H Br Br CH₃ I i-Pr H Br Br Cl I i-Pr H Br BrCH₃ I t-Bu H Br Br Cl I t-Bu H Br Br CH₃ I Me Me Br Br Cl I Me Me ClOCH₂CF₃ CH₃ I Me H Cl OCH₂CF₃ Cl I Me H Cl OCH₂CF₃ CH₃ I Et H Cl OCH₂CF₃Cl I Et H Cl OCH₂CF₃ CH₃ I i-Pr H Cl OCH₂CF₃ Cl I i-Pr H Cl OCH₂CF₃ CH₃I t-Bu H Cl OCH₂CF₃ Cl I t-Bu H Cl OCH₂CF₃ CH₃ I Me Me Cl OCH₂CF₃ Cl IMe Me Br OCH₂CF₃ CH₃ I Me U Br OCH₂CF₃ Cl I Me H Br OCH₂CF₃ CH₃ I Et UBr OCH₂CF₃ Cl I Et H Br OCH₂CF₃ CH₃ I i-Pr H Br OCH₂CF₃ Cl I i-Pr H BrOCH₂CF₃ CH₃ I t-Bu H Br OCH₂CF₃ Cl I t-Bu H Br OCH₂CF₃ CH₃ I Me Me BrOCH₂CF₃ Cl I Me Me Cl CF₃ CH₃ CF₃ Me H Cl CF₃ Cl CF₃ Me H Cl CF₃ CH₃ CF₃Et H Cl CF₃ Cl CF₃ Et H Cl CF₃ CH₃ CF₃ i-Pr H Cl CF₃ Cl CF₃ i-Pr H ClCF₃ CH₃ CF₃ t-Bu H Cl CF₃ Cl CF₃ t-Bu H Cl CF₃ CH₃ CF₃ Me Me Cl CF₃ ClCF₃ Me Me Br CF₃ CH₃ CF₃ Me H Br CF₃ Cl CF₃ Me H Br CF₃ CH₃ CF₃ Et H BrCF₃ Cl CF₃ Et H Br CF₃ CH₃ CF₃ i-Pr H Br CF₃ Cl CF₃ i-Pr H Br CF₃ CH₃CF₃ t-Bu H Br CF₃ Cl CF₃ t-Bu H Br CF₃ CH₃ CF₃ Me Me Br CF₃ Cl CF₃ Me MeCl Cl CH₃ CF₃ Me H Cl Cl Cl CF₃ Me H Cl Cl CH₃ CF₃ Et H Cl Cl Cl CF₃ EtH Cl Cl CH₃ CF₃ i-Pr H Cl Cl Cl CF₃ i-Pr H Cl Cl CH₃ CF₃ t-Bu H Cl Cl ClCF₃ t-Bu H Cl Cl CH₃ CF₃ Me Me Cl Cl Cl CF₃ Me Me Br Cl CH₃ CF₃ Me H BrCl Cl CF₃ Me H Br Cl CH₃ CF₃ Et H Br Cl Cl CF₃ Et H Br Cl CH₃ CF₃ i-Pr HBr Cl Cl CF₃ i-Pr H Br Cl CH₃ CF₃ t-Bu H Br Cl Cl CF₃ t-Bu H Br Cl CH₃CF₃ Me Me Br Cl Cl CF₃ Me Me Cl Br CH₃ CF₃ Me H Cl Br Cl CF₃ Me H Cl BrCH₃ CF₃ Et H Cl Br Cl CF₃ Et H Cl Br CH₃ CF₃ i-Pr H Cl Br Cl CF₃ i-Pr HCl Br CH₃ CF₃ t-Bu H Cl Br Cl CF₃ t-Bu H Cl Br CH₃ CF₃ Me Me Cl Br ClCF₃ Me Me Br Br CH₃ CF₃ Me H Br Br Cl CF₃ Me H Br Br CH₃ CF₃ Et H Br BrCl CF₃ Et H Br Br CH₃ CF₃ i-Pr H Br Br Cl CF₃ i-Pr H Br Br CH₃ CF₃ t-BuH Br Br Cl CF₃ t-Bu H Br Br CH₃ CF₃ Me Me Br Br Cl CF₃ Me Me Cl OCH₂CF₃CH₃ CF₃ Me H Cl OCH₂CF₃ Cl CF₃ Me H Cl OCH₂CF₃ CH₃ CF₃ Et H Cl OCH₂CF₃Cl CF₃ Et H Cl OCH₂CF₃ CH₃ CF₃ i-Pr H Cl OCH₂CF₃ Cl CF₃ i-Pr H ClOCH₂CF₃ CH₃ CF₃ t-Bu H Cl OCH₂CF₃ Cl CF₃ t-Bu H Cl OCH₂CF₃ CH₃ CF₃ Me MeCl OCH₂CF₃ Cl CF₃ Me Me Br OCH₂CF₃ CH₃ CF₃ Me H Br OCH₂CF₃ Cl CF₃ Me HBr OCH₂CF₃ CH₃ CF₃ Et H Br OCH₂CF₃ Cl CF₃ Et H Br OCH₂CF₃ CH₃ CF₃ i-Pr HBr OCH₂CF₃ Cl CF₃ i-Pr H Br OCH₂CF₃ CH₃ CF₃ t-Bu H Br OCH₂CF₃ Cl CF₃t-Bu H Br OCH₂CF₃ CH₃ CF₃ Me Me Br OCH₂CF₃ Cl CF₃ Me Me Cl Cl CH₃ Cln-Pr H Cl Cl Cl Cl n-Pr H Cl Cl CH₃ Cl n-Bu H Cl Cl Cl Cl n-Bu H Cl ClCH₃ Cl s-Bu H Cl Cl Cl Cl s-Bu H Cl Cl CH₃ Cl i-Bu H Cl Cl Cl Cl i-Bu HCl Cl CH₃ Cl Et Me Cl Cl Cl Cl Et Et Cl CF₃ F H Me H Cl CF₃ Br H Me H ClCF₃ F H Et H Cl CF₃ Br H Et H Cl CF₃ F H i-Pr H Cl CF₃ Br H i-Pr H ClCF₃ F H t-Bu H Cl CF₃ Br H t-Bu H Cl CF₃ F H Me Me Cl CF₃ Br H Me Me BrCF₃ F H Me H Br CF₃ Br H Me H Br CF₃ F H Et H Br CF₃ Br H Et H Br CF₃ FH i-Pr H Br CF₃ Br H i-Pr H Br CF₃ F H t-Bu H Br CF₃ Br H t-Bu H Br CF₃F H Me Me Br CF₃ Br H Me Me Cl Cl F H Me H Cl Cl Br H Me H Cl Cl F H EtH Cl Cl Br H Et H Cl Cl F H i-Pr H Cl Cl Br H i-Pr H Cl Cl F H t-Bu H ClCl Br H t-Bu H Cl Cl F H Me Me Cl Cl Br H Me Me Br Cl F H Me H Br Cl BrH Me H Br Cl F H Et H Br Cl Br H Et H Br Cl F H i-Pr H Br Cl Br H i-Pr HBr Cl F H t-Bu H Br Cl Br H t-Bu H Br Cl F H Me Me Br Cl Br H Me Me ClBr F H Me H Cl Br Br H Me H Cl Br F H Et H Cl Br Br H Et H Cl Br F Hi-Pr H Cl Br Br H i-Pr H Cl Br F H t-Bu H Cl Br Br H t-Bu H Cl Br F H MeMe Cl Br Br H Me Me Br Br F H Me H Br Br Br H Me H Br Br F H Et H Br BrBr H Et H Br Br F H i-Pr H Br Br Br H i-Pr H Br Br F H t-Bu H Br Br Br Ht-Bu H Br Br F H Me Me Br Br Br H Me Me Cl OCH₂CF₃ F H Me H Cl OCH₂CF₃Br H Me H Cl OCH₂CF₃ F H Et H Cl OCH₂CF₃ Br H Et H Cl OCH₂CF₃ F H i-Pr HCl OCH₂CF₃ Br H i-Pr H Cl OCH₂CF₃ F H t-Bu H Cl OCH₂CF₃ Br H t-Bu H ClOCH₂CF₃ F H Me Me Cl OCH₂CF₃ Br H Me Me Br OCH₂CF₃ F H Me H Br OCH₂CF₃Br H Me H Br OCH₂CF₃ F H Et H Br OCH₂CF₃ Br H Et H Br OCH₂CF₃ F H i-Pr HBr OCH₂CF₃ Br H i-Pr H Br OCH₂CF₃ F H t-Bu H Br OCH₂CF₃ Br H t-Bu H BrOCH₂CF₃ F H Me Me Br OCH₂CF₃ Br H Me Me Cl CF₃ F F Me H Cl CF₃ Br F Me HCl CF₃ F F Et H Cl CF₃ Br F Et H Cl CF₃ F F I-Pr H Cl CF₃ Br F i-Pr H ClCF₃ F F t-Bu H Cl CF₃ Br F t-Bu H Cl CF₃ F F Me Me Cl CF₃ Br F Me Me BrCF₃ F F Me H Br CF₃ Br F Me H Br CF₃ F F Et H Br CF₃ Br F Et H Br CF₃ FF i-Pr H Br CF₃ Br F i-Pr H Br CF₃ F F t-Bu H Br CF₃ Br F t-Bu H Br CF₃F F Me Me Br CF₃ Br F Me Me Cl Cl F F Me H Cl Cl Br F Me H Cl Cl F F EtH Cl Cl Br F Et H Cl Cl F F i-Pr H Cl Cl Br F i-Pr H Cl Cl F F t-Bu H ClCl Br F t-Bu H Cl Cl F F Me Me Cl Cl Br F Me Me Br Cl F F Me H Br Cl BrF Me H Br Cl F F Et H Br Cl Br F Et H Br Cl F F i-Pr H Br Cl Br F i-Pr HBr Cl F F t-Bu H Br Cl Br F t-Bu H Br Cl F F Me Me Br Cl Br F Me Me ClBr F F Me H Cl Br Br F Me H Cl Br F F Et H Cl Br Br F Et H Cl Br F Fi-Pr H Cl Br Br F i-Pr H Cl Br F F t-Bu H Cl Br Br F t-Bu H Cl Br F F MeMe Cl Br Br F Me Me Br Br F F Me H Br Br Br F Me H Br Br F F Et H Br BrBr F Et H Br Br F F i-Pr H Br Br Br F i-Pr H Br Br F F t-Bu H Br Br Br Ft-Bu H Br Br F F Me Me Br Br Br F Me Me Cl OCH₂CF₃ F F Me H Cl OCH₂CF₃Br F Me H Cl OCH₂CF₃ F F Et H Cl OCH₂CF₃ Br F Et H Cl OCH₂CF₃ F F i-Pr HCl OCH₂CF₃ Br F i-Pr H Cl OCH₂CF₃ F F t-Bu H Cl OCH₂CF₃ Br F t-Bu H ClOCH₂CF₃ F F Me Me Cl OCH₂CF₃ Br F Me Me Br OCH₂CF₃ F F Me H Br OCH₂CF₃Br F Me H Br OCH₂CF₃ F F Et H Br OCH₂CF₃ Br F Et H Br OCH₂CF₃ F F i-Pr HBr OCH₂CF₃ Br F i-Pr H Br OCH₂CF₃ F F t-Bu H Br OCH₂CF₃ Br F t-Bu H BrOCH₂CF₃ F F Me Me Br OCH₂CF₃ Br F Me Me Cl CF₃ F Cl Me H Cl CF₃ Br Cl MeH Cl CF₃ F Cl Et H Cl CF₃ Br Cl Et H Cl CF₃ F Cl i-Pr H Cl CF₃ Br Cli-Pr H Cl CF₃ F Cl t-Bu H Cl CF₃ Br Cl t-Bu H Cl CF₃ F Cl Me Me Cl CF₃Br Cl Me Me Br CF₃ F Cl Me H Br CF₃ Br Cl Me H Br CF₃ F Cl Et H Br CF₃Br Cl Et H Br CF₃ F Cl i-Pr H Br CF₃ Br Cl i-Pr H Br CF₃ F Cl t-Bu H BrCF₃ Br Cl t-Bu H Br CF₃ F Cl Me Me Br CF₃ Br Cl Me Me Cl Cl F Cl Me H ClCl Br Cl Me H Cl Cl F Cl Et H Cl Cl Br Cl Et H Cl Cl F Cl i-Pr H Cl ClBr Cl i-Pr H Cl Cl F Cl t-Bu H Cl Cl Br Cl t-Bu H Cl Cl F Cl Me Me Cl ClBr Cl Me Me Br Cl F Cl Me H Br Cl Br Cl Me H Br Cl F Cl Et H Br Cl Br ClEt H Br Cl F Cl i-Pr H Br Cl Br Cl i-Pr H Br Cl F Cl t-Bu H Br Cl Br Clt-Bu H Br Cl F Cl Me Me Br Cl Br Cl Me Me Cl Br F Cl Me H Cl Br Br Cl MeH Cl Br F Cl Et H Cl Br Br Cl Et H Cl Br F Cl i-Pr H Cl Br Br Cl i-Pr HCl Br F Cl t-Bu H Cl Br Br Cl t-Bu H Cl Br F Cl Me Me Cl Br Br Cl Me MeBr Br F Cl Me H Br Br Br Cl Me H Br Br F Cl Et H Br Br Br Cl Et H Br BrF Cl i-Pr H Br Br Br Cl i-Pr H Br Br F Cl t-Bu H Br Br Br Cl t-Bu H BrBr F Cl Me Me Br Br Br Cl Me Me Cl OCH₂CF₃ F Cl Me H Cl OCH₂CF₃ Br Cl MeH Cl OCH₂CF₃ F Cl Et H Cl OCH₂CF₃ Br Cl Et H Cl OCH₂CF₃ F Cl i-Pr H ClOCH₂CF₃ Br Cl i-Pr H Cl OCH₂CF₃ F Cl t-Bu H Cl OCH₂CF₃ Br Cl t-Bu H ClOCH₂CF₃ F Cl Me Me Cl OCH₂CF₃ Br Cl Me Me Br OCH₂CF₃ F Cl Me H BrOCH₂CF₃ Br Cl Me H Br OCH₂CF₃ F Cl Et H Br OCH₂CF₃ Br Cl Et H Br OCH₂CF₃F Cl i-Pr H Br OCH₂CF₃ Br Cl i-Pr H Br OCH₂CF₃ F Cl t-Bu H Br OCH₂CF₃ BrCl t-Bu H Br OCH₂CF₃ F Cl Me Me Br OCH₂CF₃ Br Cl Me Me Cl CF₃ F Br Me HCl CF₃ Br Br Me H Cl CF₃ F Br Et H Cl CF₃ Br Br Et H Cl CF₃ F Br i-Pr HCl CF₃ Br Br i-Pr H Cl CF₃ F Br t-Bu H Cl CF₃ Br Br t-Bu H Cl CF₃ F BrMe Me Cl CF₃ Br Br Me Me Br CF₃ F Br Me H Br CF₃ Br Br Me H Br CF₃ F BrEt H Br CF₃ Br Br Et H Br CF₃ F Br i-Pr H Br CF₃ Br Br i-Pr H Br CF₃ FBr t-Bu H Br CF₃ Br Br t-Bu H Br CF₃ F Br Me Me Br CF₃ Br Br Me Me Cl ClF Br Me H Cl Cl Br Br Me H Cl Cl F Br Et H Cl Cl Br Br Et H Cl Cl F Bri-Pr H Cl Cl Br Br i-Pr H Cl Cl F Br t-Bu H Cl Cl Br Br t-Bu H Cl Cl FBr Me Me Cl Cl Br Br Me Me Br Cl F Br Me H Br Cl Br Br Me H Br Cl F BrEt H Br Cl Br Br Et H Br Cl F Br i-Pr H Br Cl Br Br i-Pr H Br Cl F Brt-Bu H Br Cl Br Br t-Bu H Br Cl F Br Me Me Br Cl Br Br Me Me Cl Br F BrMe H Cl Br Br Br Me H Cl Br F Br Et H Cl Br Br Br Et H Cl Br F Br i-Pr HCl Br Br Br i-Pr H Cl Br F Br t-Bu H Cl Br Br Br t-Bu H Cl Br F Br Me MeCl Br Br Br Me Me Br Br F Br Me H Br Br Br Br Me H Br Br F Br Et H Br BrBr Br Et H Br Br F Br i-Pr H Br Br Br Br i-Pr H Br Br F Br t-Bu H Br BrBr Br t-Bu H Br Br F Br Me Me Br Br Br Br Me Me Cl OCH₂CF₃ F Br Me H ClOCH₂CF₃ Br Br Me H Cl OCH₂CF₃ F Br Et H Cl OCH₂CF₃ Br Br Et H Cl OCH₂CF₃F Br i-Pr H Cl OCH₂CF₃ Br Br i-Pr H Cl OCH₂CF₃ F Br t-Bu H Cl OCH₂CF₃ BrBr t-Bu H Cl OCH₂CF₃ F Br Me Me Cl OCH₂CF₃ Br Br Me Me Br OCH₂CF₃ F BrMe H Br OCH₂CF₃ Br Br Me H Br OCH₂CF₃ F Br Et H Br OCH₂CF₃ Br Br Et H BrOCH₂CF₃ F Br i-Pr H Br OCH₂CF₃ Br Br i-Pr H Br OCH₂CF₃ F Br t-Bu H BrOCH₂CF₃ Br Br t-Bu H Br OCH₂CF₃ F Br Me Me Br OCH₂CF₃ Br Br Me Me Cl CF₃F I Me H Cl CF₃ Br I Me H Cl CF₃ F I Et H Cl CF₃ Br I Et H Cl CF₃ F Ii-Pr H Cl CF₃ Br I i-Pr H Cl CF₃ F I t-Bu H Cl CF₃ Br I t-Bu H Cl CF₃ FI Me Me Cl CF₃ Br I Me Me Br CF₃ F I Me H Br CF₃ Br I Me H Br CF₃ F I EtH Br CF₃ Br I Et H Br CF₃ F I i-Pr H Br CF₃ Br I i-Pr H Br CF₃ F I t-BuH Br CF₃ Br I t-Bu H Br CF₃ F I Me Me Br CF₃ Br I Me Me Cl Cl F I Me HCl Cl Br I Me H Cl Cl F I Et H Cl Cl Br I Et H Cl Cl F I i-Pr H Cl Cl BrI i-Pr H Cl Cl F I t-Bu H Cl Cl Br I t-Bu H Cl Cl F I Me Me Cl Cl Br IMe Me Br Cl F I Me H Br Cl Br I Me H Br Cl F I Et H Br Cl Br I Et H BrCl F I i-Pr H Br Cl Br I i-Pr H Br Cl F I t-Bu H Br Cl Br I t-Bu H Br ClF I Me Me Br Cl Br I Me Me Cl Br F I Me H Cl Br Br I Me H Cl Br F I Et HCl Br Br I Et H Cl Br F I i-Pr H Cl Br Br I i-Pr H Cl Br F I t-Bu H ClBr Br I t-Bu H Cl Br F I Me Me Cl Br Br I Me Me Br Br F I Me H Br Br BrI Me H Br Br F I Et H Br Br Br I Et H Br Br F I i-Pr H Br Br Br I i-Pr HBr Br F I t-Bu H Br Br Br I t-Bu H Br Br F I Me Me Br Br Br I Me Me ClOCH₂CF₃ F I Me H Cl OCH₂CF₃ Br I Me H Cl OCH₂CF₃ F I Et H Cl OCH₂CF₃ BrI Et H Cl OCH₂CF₃ F I i-Pr H Cl OCH₂CF₃ Br I i-Pr H Cl OCH₂CF₃ F I t-BuH Cl OCH₂CF₃ Br I t-Bu H Cl OCH₂CF₃ F I Me Me Cl OCH₂CF₃ Br I Me Me BrOCH₂CF₃ F I Me H Br OCH₂CF₃ Br I Me H Br OCH₂CF₃ F I Et H Br OCH₂CF₃ BrI Et H Br OCH₂CF₃ F I i-Pr H Br OCH₂CF₃ Br I i-Pr H Br OCH₂CF₃ F I t-BuH Br OCH₂CF₃ Br I t-Bu H Br OCH₂CF₃ F I Me Me Br OCH₂CF₃ Br I Me Me ClCF₃ F CF₃ Me H Cl CF₃ Br CF₃ Me H Cl CF₃ F CF₃ Et H Cl CF₃ Br CF₃ Et HCl CF₃ F CF₃ i-Pr H Cl CF₃ Br CF₃ i-Pr H Cl CF₃ F CF₃ t-Bu H Cl CF₃ BrCF₃ t-Bu H Cl CF₃ F CF₃ Me Me Cl CF₃ Br CF₃ Me Me Br CF₃ F CF₃ Me H BrCF₃ Br CF₃ Me H Br CF₃ F CF₃ Et H Br CF₃ Br CF₃ Et H Br CF₃ F CF₃ i-Pr HBr CF₃ Br CF₃ i-Pr H Br CF₃ F CF₃ t-Bu H Br CF₃ Br CF₃ t-Bu H Br CF₃ FCF₃ Me Me Br CF₃ Br CF₃ Me Me Cl Cl F CF₃ Me H Cl Cl Br CF₃ Me H Cl Cl FCF₃ Et H Cl Cl Br CF₃ Et H Cl Cl F CF₃ i-Pr H Cl Cl Br CF₃ i-Pr H Cl ClF CF₃ t-Bu H Cl Cl Br CF₃ t-Bu H Cl Cl F CF₃ Me Me Cl Cl Br CF₃ Me Me BrCl F CF₃ Me H Br Cl Br CF₃ Me H Br Cl F CF₃ Et H Br Cl Br CF₃ Et H Br ClF CF₃ i-Pr H Br Cl Br CF₃ i-Pr H Br Cl F CF₃ t-Bu H Br Cl Br CF₃ t-Bu HBr Cl F CF₃ Me Me Br Cl Br CF₃ Me Me Cl Br F CF₃ Me H Cl Br Br CF₃ Me HCl Br F CF₃ Et H Cl Br Br CF₃ Et H Cl Br F CF₃ i-Pr H Cl Br Br CF₃ i-PrH Cl Br F CF₃ t-Bu H Cl Br Br CF₃ t-Bu H Cl Br F CF₃ Me Me Cl Br Br CF₃Me Me Br Br F CF₃ Me H Br Br Br CF₃ Me H Br Br F CF₃ Et H Br Br Br CF₃Et H Br Br F CF₃ i-Pr H Br Br Br CF₃ i-Pr H Br Br F CF₃ t-Bu H Br Br BrCF₃ t-Bu H Br Br F CF₃ Me Me Br Br Br CF₃ Me Me Cl OCH₂CF₃ F CF₃ Me H ClOCH₂CF₃ Br CF₃ Me H Cl OCH₂CF₃ F CF₃ Et H Cl OCH₂CF₃ Br CF₃ Et H ClOCH₂CF₃ F CF₃ i-Pr H Cl OCH₂CF₃ Br CF₃ i-Pr H Cl OCH₂CF₃ F CF₃ t-Bu H ClOCH₂CF₃ Br CF₃ t-Bu H Cl OCH₂CF₃ F CF₃ Me Me Cl OCH₂CF₃ Br CF₃ Me Me BrOCH₂CF₃ F CF₃ Me H Br OCH₂CF₃ Br CF₃ Me H Br OCH₂CF₃ F CF₃ Et H BrOCH₂CF₃ Br CF₃ Et H Br OCH₂CF₃ F CF₃ i-Pr H Br OCH₂CF₃ Br CF₃ i-Pr H BrOCH₂CF₃ F CF₃ t-Bu H Br OCH₂CF₃ Br CF₃ t-Bu H Br OCH₂CF₃ F CF₃ Me Me BrOCH₂CF₃ Br CF₃ Me Me

[0254] TABLE 2

R⁶(a) R⁵(a) R⁴(a) R⁴(b) R³ R² R⁶(a) R⁵(a) R⁴(a) R⁴(b) R³ R² Cl CF₃ CH₃ HMe H Cl CF₃ Cl H Me H Cl CF₃ CH₃ H Et H Cl CF₃ Cl H Et H Cl CF₃ CH₃ Hi-Pr H Cl CF₃ Cl H i-Pr H Cl CF₃ CH₃ H t-Bu H Cl CF₃ Cl H t-Bu H Cl CF₃CH₃ H Me Me Cl CF₃ Cl H Me Me Br CF₃ CH₃ H Me H Br CF₃ Cl H Me H Br CF₃CH₃ H Et H Br CF₃ Cl H Et H Br CF₃ CH₃ H i-Pr H Br CF₃ Cl H i-Pr H BrCF₃ CH₃ H t-Bu H Br CF₃ Cl H t-Bu H Br CF₃ CH₃ H Me Me Br CF₃ Cl H Me MeCl Cl CH₃ H Me H Cl Cl Cl H Me H Cl Cl CH₃ H Et H Cl Cl Cl H Et H Cl ClCH₃ H i-Pr H Cl Cl Cl H i-Pr H Cl Cl CH₃ H t-Bu H Cl Cl Cl H t-Bu H ClCl CH₃ H Me Me Cl Cl Cl H Me Me Br Cl CH₃ H Me H Br Cl Cl H Me H Br ClCH₃ H Et H Br Cl Cl H Et H Br Cl CH₃ H i-Pr H Br Cl Cl H i-Pr H Br ClCH₃ H t-Bu H Br Cl Cl H t-Bu H Br Cl CH₃ H Me Me Br Cl Cl H Me Me Cl BrCH₃ H Me H Cl Br Cl H Me H Cl Br CH₃ H Et H Cl Br Cl H Et H Cl Br CH₃ Hi-Pr H Cl Br Cl H i-Pr H Cl Br CH₃ H t-Bu H Cl Br Cl H t-Bu H Cl Br CH₃H Me Me Cl Br Cl H Me Me Br Br CH₃ H Me H Br Br Cl H Me H Br Br CH₃ H EtH Br Br Cl H Et H Br Br CH₃ H i-Pr H Br Br Cl H i-Pr H Br Br CH₃ H t-BuH Br Br Cl H t-Bu H Br Br CH₃ H Me Me Br Br Cl H Me Me Cl OCH₂CF₃ CH₃ HMe H Cl OCH₂CF₃ Cl H Me H Cl OCH₂CF₃ CH₃ H Et H Cl OCH₂CF₃ Cl H Et H ClOCH₂CF₃ CH₃ H i-Pr H Cl OCH₂CF₃ Cl H i-Pr H Cl OCH₂CF₃ CH₃ H t-Bu H ClOCH₂CF₃ Cl H t-Bu H Cl OCH₂CF₃ CH₃ H Me Me Cl OCH₂CF₃ Cl H Me Me BrOCH₂CF₃ CH₃ H Me H Br OCH₂CF₃ Cl H Me H Br OCH₂CF₃ CH₃ H Et H Br OCH₂CF₃Cl H Et H Br OCH₂CF₃ CH₃ H i-Pr H Br OCH₂CF₃ Cl H i-Pr H Br OCH₂CF₃ CH₃H t-Bu H Br OCH₂CF₃ Cl H t-Bu H Br OCH₂CF₃ CH₃ H Me Me Br OCH₂CF₃ Cl HMe Me Cl CF₃ CH₃ F Me H Cl CF₃ Cl F Me H Cl CF₃ CH₃ F Et H Cl CF₃ Cl FEt H Cl CF₃ CH₃ F i-Pr H Cl CF₃ Cl F i-Pr H Cl CF₃ CH₃ F t-Bu H Cl CF₃Cl F t-Bu H Cl CF₃ CH₃ F Me Me Cl CF₃ Cl F Me Me Br CF₃ CH₃ F Me H BrCF₃ Cl F Me H Br CF₃ CH₃ F Et H Br CF₃ Cl F Et H Br CF₃ CH₃ F i-Pr H BrCF₃ Cl F i-Pr H Br CF₃ CH₃ F t-Bu H Br CF₃ Cl F t-Bu H Br CF₃ CH₃ F MeMe Br CF₃ Cl F Me Me Cl Cl CH₃ F Me H Cl Cl Cl F Me H Cl Cl CH₃ F Et HCl Cl Cl F Et H Cl Cl CH₃ F i-Pr H Cl Cl Cl F i-Pr H Cl Cl CH₃ F t-Bu HCl Cl Cl F t-Bu H Cl Cl CH₃ F Me Me Cl Cl Cl F Me Me Br Cl CH₃ F Me H BrCl Cl F Me H Br Cl CH₃ F Et H Br Cl Cl F Et H Br Cl CH₃ F i-Pr H Br ClCl F i-Pr H Br Cl CH₃ F t-Bu H Br Cl Cl F t-Bu H Br Cl CH₃ F Me Me Br ClCl F Me Me Cl Br CH₃ F Me H Cl Br Cl F Me H Cl Br CH₃ F Et H Cl Br Cl FEt H Cl Br CH₃ F i-Pr H Cl Br Cl F i-Pr H Cl Br CH₃ F t-Bu H Cl Br Cl Ft-Bu H Cl Br CH₃ F Me Me Cl Br Cl F Me Me Br Br CH₃ F Me H Br Br Cl F MeH Br Br CH₃ F Et H Br Br Cl F Et H Br Br CH₃ F i-Pr H Br Br Cl F i-Pr HBr Br CH₃ F t-Bu H Br Br Cl F t-Bu H Br Br CH₃ F Me Me Br Br Cl F Me MeCl OCH₂CF₃ CH₃ F Me H Cl OCH₂CF₃ Cl F Me H Cl OCH₂CF₃ CH₃ F Et H ClOCH₂CF₃ Cl F Et H Cl OCH₂CF₃ CH₃ F i-Pr H Cl OCH₂CF₃ Cl F i-Pr H ClOCH₂CF₃ CH₃ F t-Bu H Cl OCH₂CF₃ Cl F t-Bu H Cl OCH₂CF₃ CH₃ F Me Me ClOCH₂CF₃ Cl F Me Me Br OCH₂CF₃ CH₃ F Me H Br OCH₂CF₃ Cl F Me H Br OCH₂CF₃CH₃ F Et H Br OCH₂CF₃ Cl F Et H Br OCH₂CF₃ CH₃ F i-Pr H Br OCH₂CF₃ Cl Fi-Pr H Br OCH₂CF₃ CH₃ F t-Bu H Br OCH₂CF₃ Cl F t-Bu H Br OCH₂CF₃ CH₃ FMe Me Br OCH₂CF₃ Cl F Me Me Cl CF₃ CH₃ Cl Me H Cl CF₃ Cl Cl Me H Cl CF₃CH₃ Cl Et H Cl CF₃ Cl Cl Et H Cl CF₃ CH₃ Cl i-Pr H Cl CF₃ Cl Cl i-Pr HCl CF₃ CH₃ Cl t-Bu H Cl CF₃ Cl Cl t-Bu H Cl CF₃ CH₃ Cl Me Me Cl CF₃ ClCl Me Me Br CF₃ CH₃ Cl Me H Br CF₃ Cl Cl Me H Br CF₃ CH₃ Cl Et H Br CF₃Cl Cl Et H Br CF₃ CH₃ Cl i-Pr H Br CF₃ Cl Cl i-Pr H Br CF₃ CH₃ Cl t-Bu HBr CF₃ Cl Cl t-Bu H Br CF₃ CH₃ Cl Me Me Br CF₃ Cl Cl Me Me Cl Cl CH₃ ClMe H Cl Cl Cl Cl Me H Cl Cl CH₃ Cl Et H Cl Cl Cl Cl Et H Cl Cl CH₃ Cli-Pr H Cl Cl Cl Cl i-Pr H Cl Cl CH₃ Cl t-Bu H Cl Cl Cl Cl t-Bu H Cl ClCH₃ Cl Me Me Cl Cl Cl Cl Me Me Br Cl CH₃ Cl Me H Br Cl Cl Cl Me H Br ClCH₃ Cl Et H Br Cl Cl Cl Et H Br Cl CH₃ Cl i-Pr H Br Cl Cl Cl i-Pr H BrCl CH₃ Cl t-Bu H Br Cl Cl Cl t-Bu H Br Cl CH₃ Cl Me Me Br Cl Cl Cl Me MeCl Br CH₃ Cl Me H Cl Br Cl Cl Me H Cl Br CH₃ Cl Et H Cl Br Cl Cl Et H ClBr CH₃ Cl i-Pr H Cl Br Cl Cl i-Pr H Cl Br CH₃ Cl t-Bu H Cl Br Cl Cl t-BuH Cl Br CH₃ Cl Me Me Cl Br Cl Cl Me Me Br Br CH₃ Cl Me H Br Br Cl Cl MeH Br Br CH₃ Cl Et H Br Br Cl Cl Et H Br Br CH₃ Cl i-Pr H Br Br Cl Cli-Pr H Br Br CH₃ Cl t-Bu H Br Br Cl Cl t-Bu H Br Br CH₃ Cl Me Me Br BrCl Cl Me Me Cl OCH₂CF₃ CH₃ Cl Me H Cl OCH₂CF₃ Cl Cl Me H Cl OCH₂CF₃ CH₃Cl Et H Cl OCH₂CF₃ Cl Cl Et H Cl OCH₂CF₃ CH₃ Cl i-Pr H Cl OCH₂CF₃ Cl Cli-Pr H Cl OCH₂CF₃ CH₃ Cl t-Bu H Cl OCH₂CF₃ Cl Cl t-Bu H Cl OCH₂CF₃ CH₃Cl Me Me Cl OCH₂CF₃ Cl Cl Me Me Br OCH₂CF₃ CH₃ Cl Me H Br OCH₂CF₃ Cl ClMe H Br OCH₂CF₃ CH₃ Cl Et H Br OCH₂CF₃ Cl Cl Et H Br OCH₂CF₃ CH₃ Cl i-PrH Br OCH₂CF₃ Cl Cl i-Pr H Br OCH₂CF₃ CH₃ Cl t-Bu H Br OCH₂CF₃ Cl Cl t-BuH Br OCH₂CF₃ CH₃ Cl Me Me Br OCH₂CF₃ Cl Cl Me Me Cl CF₃ CH₃ Br Me H ClCF₃ Cl Br Me H Cl CF₃ CH₃ Br Et H Cl CF₃ Cl Br Et H Cl CF₃ CH₃ Br i-Pr HCl CF₃ Cl Br i-Pr H Cl CF₃ CH₃ Br t-Bu H Cl CF₃ Cl Br t-Bu H Cl CF₃ CH₃Br Me Me Cl CF₃ Cl Br Me Me Br CF₃ CH₃ Br Me H Br CF₃ Cl Br Me H Br CF₃CH₃ Br Et H Br CF₃ Cl Br Et H Br CF₃ CH₃ Br i-Pr H Br CF₃ Cl Br i-Pr HBr CF₃ CH₃ Br t-Bu H Br CF₃ Cl Br t-Bu H Br CF₃ CH₃ Br Me Me Br CF₃ ClBr Me Me Cl Cl CH₃ Br Me H Cl Cl Cl Br Me H Cl Cl CH₃ Br Et H Cl Cl ClBr Et H Cl Cl CH₃ Br i-Pr H Cl Cl Cl Br i-Pr H Cl Cl CH₃ Br t-Bu H Cl ClCl Br t-Bu H Cl Cl CH₃ Br Me Me Cl Cl Cl Br Me Me Br Cl CH₃ Br Me H BrCl Cl Br Me H Br Cl CH₃ Br Et H Br Cl Cl Br Et H Br Cl CH₃ Br i-Pr H BrCl Cl Br i-Pr H Br Cl CH₃ Br t-Bu H Br Cl Cl Br t-Bu H Br Cl CH₃ Br MeMe Br Cl Cl Br Me Me Cl Br CH₃ Br Me H Cl Br Cl Br Me H Cl Br CH₃ Br EtH Cl Br Cl Br Et H Cl Br CH₃ Br i-Pr H Cl Br Cl Br i-Pr H Cl Br CH₃ Brt-Bu H Cl Br Cl Br t-Bu H Cl Br CH₃ Br Me Me Cl Br Cl Br Me Me Br Br CH₃Br Me H Br Br Cl Br Me H Br Br CH₃ Br Et H Br Br Cl Br Et H Br Br CH₃ Bri-Pr H Br Br Cl Br i-Pr H Br Br CH₃ Br t-Bu H Br Br Cl Br t-Bu H Br BrCH₃ Br Me Me Br Br Cl Br Me Me Cl OCH₂CF₃ CH₃ Br Me H Cl OCH₂CF₃ Cl BrMe H Cl OCH₂CF₃ CH₃ Br Et H Cl OCH₂CF₃ Cl Br Et H Cl OCH₂CF₃ CH₃ Br i-PrH Cl OCH₂CF₃ Cl Br i-Pr H Cl OCH₂CF₃ CH₃ Br t-Bu H Cl OCH₂CF₃ Cl Br t-BuH Cl OCH₂CF₃ CH₃ Br Me Me Cl OCH₂CF₃ Cl Br Me Me Br OCH₂CF₃ CH₃ Br Me HBr OCH₂CF₃ Cl Br Me H Br OCH₂CF₃ CH₃ Br Et H Br OCH₂CF₃ Cl Br Et H BrOCH₂CF₃ CH₃ Br i-Pr H Br OCH₂CF₃ Cl Br i-Pr H Br OCH₂CF₃ CH₃ Br t-Bu HBr OCH₂CF₃ Cl Br t-Bu H Br OCH₂CF₃ CH₃ Br Me Me Br OCH₂CF₃ Cl Br Me MeCl CF₃ CH₃ I Me H Cl CF₃ Cl I Me H Cl CF₃ CH₃ I Et H Cl CF₃ Cl I Et H ClCF₃ CH₃ I i-Pr H Cl CF₃ Cl I i-Pr H Cl CF₃ CH₃ I t-Bu H Cl CF₃ Cl I t-BuH Cl CF₃ CH₃ I Me Me Cl CF₃ Cl I Me Me Br CF₃ CH₃ I Me H Br CF₃ Cl I MeH Br CF₃ CH₃ I Et H Br CF₃ Cl I Et H Br CF₃ CH₃ I i-Pr H Br CF₃ Cl Ii-Pr H Br CF₃ CH₃ I t-Bu H Br CF₃ Cl I t-Bu H Br CF₃ CH₃ I Me Me Br CF₃Cl I Me Me Cl Cl CH₃ I Me H Cl Cl Cl I Me H Cl Cl CH₃ I Et H Cl Cl Cl IEt H Cl Cl CH₃ I i-Pr H Cl Cl Cl I i-Pr H Cl Cl CH₃ I t-Bu H Cl Cl Cl It-Bu H Cl Cl CH₃ I Me Me Cl Cl Cl I Me Me Br Cl CH₃ I Me H Br Cl Cl I MeH Br Cl CH₃ I Et H Br Cl Cl I Et H Br Cl CH₃ I i-Pr H Br Cl Cl I i-Pr HBr Cl CH₃ I t-Bu H Br Cl Cl I t-Bu H Br Cl CH₃ I Me Me Br Cl Cl I Me MeCl Br CH₃ I Me H Cl Br Cl I Me H Cl Br CH₃ I Et H Cl Br Cl I Et H Cl BrCH₃ I i-Pr H Cl Br Cl I i-Pr H Cl Br CH₃ I t-Bu H Cl Br Cl I t-Bu H ClBr CH₃ I Me Me Cl Br Cl I Me Me Br Br CH₃ I Me H Br Br Cl I Me H Br BrCH₃ I Et H Br Br Cl I Et H Br Br CH₃ I i-Pr H Br Br Cl I i-Pr H Br BrCH₃ I t-Bu H Br Br Cl I t-Bu H Br Br CH₃ I Me Me Br Br Cl I Me Me ClOCH₂CF₃ CH₃ I Me H Cl OCH₂CF₃ Cl I Me H Cl OCH₂CF₃ CH₃ I Et H Cl OCH₂CF₃Cl I Et H Cl OCH₂CF₃ CH₃ I i-Pr H Cl OCH₂CF₃ Cl I i-Pr H Cl OCH₂CF₃ CH₃I t-Bu H Cl OCH₂CF₃ Cl I t-Bu H Cl OCH₂CF₃ CH₃ I Me Me Cl OCH₂CF₃ Cl IMe Me Br OCH₂CF₃ CH₃ I Me H Br OCH₂CF₃ Cl I Me H Br OCH₂CF₃ CH₃ I Et HBr OCH₂CF₃ Cl I Et H Br OCH₂CF₃ CH₃ I i-Pr H Br OCH₂CF₃ Cl I i-Pr H BrOCH₂CF₃ CH₃ I t-Bu H Br OCH₂CF₃ Cl I t-Bu H Br OCH₂CF₃ CH₃ I Me Me BrOCH₂CF₃ Cl I Me Me Cl CF₃ CH₃ CF₃ Me H Cl CF₃ Cl CF₃ Me H Cl CF₃ CH₃ CF₃Et H Cl CF₃ Cl CF₃ Et H Cl CF₃ CH₃ CF₃ i-Pr H Cl CF₃ Cl CF₃ i-Pr H ClCF₃ CH₃ CF₃ t-Bu H Cl CF₃ Cl CF₃ t-Bu H Cl CF₃ CH₃ CF₃ Me Me Cl CF₃ ClCF₃ Me Me Br CF₃ CH₃ CF₃ Me H Br CF₃ Cl CF₃ Me H Br CF₃ CH₃ CF₃ Et H BrCF₃ Cl CF₃ Et H Br CF₃ CH₃ CF₃ i-Pr H Br CF₃ Cl CF₃ i-Pr H Br CF₃ CH₃CF₃ t-Bu H Br CF₃ Cl CF₃ t-Bu H Br CF₃ CH₃ CF₃ Me Me Br CF₃ Cl CF₃ Me MeCl Cl CH₃ CF₃ Me H Cl Cl Cl CF₃ Me H Cl Cl CH₃ CF₃ Et H Cl Cl Cl CF₃ EtH Cl Cl CH₃ CF₃ i-Pr H Cl Cl Cl CF₃ i-Pr H Cl Cl CH₃ CF₃ t-Bu H Cl Cl ClCF₃ t-Bu H Cl Cl CH₃ CF₃ Me Me Cl Cl Cl CF₃ Me Me Br Cl CH₃ CF₃ Me H BrCl Cl CF₃ Me H Br Cl CH₃ CF₃ Et H Br Cl Cl CF₃ Et H Br Cl CH₃ CF₃ i-Pr HBr Cl Cl CF₃ i-Pr H Br Cl CH₃ CF₃ t-Bu H Br Cl Cl CF₃ t-Bu H Br Cl CH₃CF₃ Me Me Br Cl Cl CF₃ Me Me Cl Br CH₃ CF₃ Me H Cl Br Cl CF₃ Me H Cl BrCH₃ CF₃ Et H Cl Br Cl CF₃ Et H Cl Br CH₃ CF₃ i-Pr H Cl Br Cl CF₃ i-Pr HCl Br CH₃ CF₃ t-Bu H Cl Br Cl CF₃ t-Bu H Cl Br CH₃ CF₃ Me Me Cl Br ClCF₃ Me Me Br Br CH₃ CF₃ Me H Br Br Cl CF₃ Me H Br Br CH₃ CF₃ Et H Br BrCl CF₃ Et H Br Br CH₃ CF₃ i-Pr H Br Br Cl CF₃ i-Pr H Br Br CH₃ CF₃ t-BuH Br Br Cl CF₃ t-Bu H Br Br CH₃ CF₃ Me Me Br Br Cl CF₃ Me Me Cl OCH₂CF₃CH₃ CF₃ Me H Cl OCH₂CF₃ Cl CF₃ Me H Cl OCH₂CF₃ CH₃ CF₃ Et H Cl OCH₂CF₃Cl CF₃ Et H Cl OCH₂CF₃ CH₃ CF₃ i-Pr H Cl OCH₂CF₃ Cl CF₃ i-Pr H ClOCH₂CF₃ CH₃ CF₃ t-Bu H Cl OCH₂CF₃ Cl CF₃ t-Bu H Cl OCH₂CF₃ CH₃ CF₃ Me MeCl OCH₂CF₃ Cl CF₃ Me Me Br OCH₂CF₃ CH₃ CF₃ Me H Br OCH₂CF₃ Cl CF₃ Me HBr OCH₂CF₃ CH₃ CF₃ Et H Br OCH₂CF₃ Cl CF₃ Et H Br OCH₂CF₃ CH₃ CF₃ i-Pr HBr OCH₂CF₃ Cl CF₃ i-Pr H Br OCH₂CF₃ CH₃ CF₃ t-Bu H Br OCH₂CF₃ Cl CF₃t-Bu H Br OCH₂CF₃ CH₃ CF₃ Me Me Br OCH₂CF₃ Cl CF₃ Me Me Cl Cl CH₃ Cln-Pr H Cl Cl Cl Cl n-Pr H Cl Cl CH₃ Cl n-Bu H Cl Cl Cl Cl n-Bu H Cl ClCH₃ Cl s-Bu H Cl Cl Cl Cl s-Bu H Cl Cl CH₃ Cl i-Bu H Cl Cl Cl Cl i-Bu HCl Cl CH₃ Cl Et Me Cl Cl Cl Cl Et Et Cl CF₃ F H Me H Cl CF₃ Br H Me H ClCF₃ F H Et H Cl CF₃ Br H Et H Cl CF₃ F H i-Pr H Cl CF₃ Br H i-Pr H ClCF₃ F H t-Bu H Cl CF₃ Br H t-Bu H Cl CF₃ F H Me Me Cl CF₃ Br H Me Me BrCF₃ F H Me H Br CF₃ Br H Me H Br CF₃ F H Et H Br CF₃ Br H Et H Br CF₃ FH i-Pr H Br CF₃ Br H i-Pr H Br CF₃ F H t-Bu H Br CF₃ Br H t-Bu H Br CF₃F H Me Me Br CF₃ Br H Me Me Cl Cl F H Me H Cl Cl Br H Me H Cl Cl F H EtH Cl Cl Br H Et H Cl Cl F H i-Pr H Cl Cl Br H i-Pr H Cl Cl F H t-Bu H ClCl Br H t-Bu H Cl Cl F H Me Me Cl Cl Br H Me Me Br Cl F H Me H Br Cl BrH Me H Br Cl F H Et H Br Cl Br H Et H Br Cl F H i-Pr H Br Cl Br H i-Pr HBr Cl F H t-Bu H Br Cl Br H t-Bu H Br Cl F H Me Me Br Cl Br H Me Me ClBr F H Me H Cl Br Br H Me H Cl Br F H Et H Cl Br Br H Et H Cl Br F Hi-Pr H Cl Br Br H i-Pr H Cl Br F H t-Bu H Cl Br Br H t-Bu H Cl Br F H MeMe Cl Br Br H Me Me Br Br F H Me H Br Br Br H Me H Br Br F H Et H Br BrBr H Et H Br Br F H i-Pr H Br Br Br H i-Pr H Br Br F H t-Bu H Br Br Br Ht-Bu H Br Br F H Me Me Br Br Br H Me Me Cl OCH₂CF₃ F H Me H Cl OCH₂CF₃Br H Me H Cl OCH₂CF₃ F H Et H Cl OCH₂CF₃ Br H Et H Cl OCH₂CF₃ F H i-Pr HCl OCH₂CF₃ Br H i-Pr H Cl OCH₂CF₃ F H t-Bu H Cl OCH₂CF₃ Br H t-Bu H ClOCH₂CF₃ F H Me Me Cl OCH₂CF₃ Br H Me Me Br OCH₂CF₃ F H Me H Br OCH₂CF₃Br H Me H Br OCH₂CF₃ F H Et H Br OCH₂CF₃ Br H Et H Br OCH₂CF₃ F H i-Pr HBr OCH₂CF₃ Br H i-Pr H Br OCH₂CF₃ F H t-Bu H Br OCH₂CF₃ Br H t-Bu H BrOCH₂CF₃ F H Me Me Br OCH₂CF₃ Br H Me Me Cl CF₃ F F Me H Cl CF₃ Br F Me HCl CF₃ F F Et H Cl CF₃ Br F Et H Cl CF₃ F F i-Pr H Cl CF₃ Br F i-Pr H ClCF₃ F F t-Bu H Cl CF₃ Br F t-Bu H Cl CF₃ F F Me Me Cl CF₃ Br F Me Me BrCF₃ F F Me H Br CF₃ Br F Me H Br CF₃ F F Et H Br CF₃ Br F Et H Br CF₃ FF i-Pr H Br CF₃ Br F i-Pr H Br CF₃ F F t-Bu H Br CF₃ Br F t-Bu H Br CF₃F F Me Me Br CF₃ Br F Me Me Cl Cl F F Me H Cl Cl Br F Me H Cl Cl F F EtH Cl Cl Br F Et H Cl Cl F F i-Pr H Cl Cl Br F i-Pr H Cl Cl F F t-Bu H ClCl Br F t-Bu H Cl Cl F F Me Me Cl Cl Br F Me Me Br Cl F F Me H Br Cl BrF Me H Br Cl F F EL H Br Cl Br F EL H Br Cl F F i-Pr H Br Cl Br F i-Pr HBr Cl F F t-Bu H Br Cl Br F t-Bu H Br Cl F F Me Me Br Cl Br F Me Me ClBr F F Me H Cl Br Br F Me H Cl Br F F Et H Cl Br Br F EL H Cl Br F Fi-Pr H Cl Br Br F i-Pr H Cl Br F F t-Bu H Cl Br Br F t-Bu H Cl Br F F MeMe Cl Br Br F Me Me Br Br F F Me H Br Br Br F Me H Br Br F F Et H Br BrBr F Et H Br Br F F i-Pr H Br Br Br F i-Pr H Br Br F F t-Bu H Br Br Br Ft-Bu H Br Br F F Me Me Br Br Br F Me Me Cl OCH₂CF₃ F F Me H Cl OCH₂CF₃Br F Me H Cl OCH₂CF₃ F F Et H Cl OCH₂CF₃ Br F Et H Cl OCH₂CF₃ F F i-Pr HCl OCH₂CF₃ Br F i-Pr H Cl OCH₂CF₃ F F t-Bu H Cl OCH₂CF₃ Br F t-Bu H ClOCH₂CF₃ F F Me Me Cl OCH₂CF₃ Br F Me Me Br OCH₂CF₃ F F Me H Br OCH₂CF₃Br F Me H Br OCH₂CF₃ F F EL H Br OCH₂CF₃ Br F EL H Br OCH₂CF₃ F F i-Pr HBr OCH₂CF₃ Br F i-Pr H Br OCH₂CF₃ F F t-Bu H Br OCH₂CF₃ Br F t-Bu H BrOCH₂CF₃ F F Me Me Br OCH₂CF₃ Br F Me Me Cl CF₃ F Cl Me H Cl CF₃ Br Cl MeH Cl CF₃ F Cl Et H Cl CF₃ Br Cl Et H Cl CF₃ F Cl i-Pr H Cl CF₃ Br Cli-Pr H Cl CF₃ F Cl t-Bu H Cl CF₃ Br Cl t-Bu H Cl CF₃ F Cl Me Me Cl CF₃Br Cl Me Me Br CF₃ F Cl Me H Br CF₃ Br Cl Me H Br CF₃ F Cl EL H Br CF₃Br Cl Et H Br CF₃ F Cl i-Pr H Br CF₃ Br Cl i-Pr H Br CF₃ F Cl t-Bu H BrCF₃ Br Cl t-Bu H Br CF₃ F Cl Me Me Br CF₃ Br Cl Me Me Cl Cl F Cl Me H ClCl Br Cl Me H Cl Cl F Cl Et H Cl Cl Br Cl Et H Cl Cl F Cl i-Pr H Cl ClBr Cl i-Pr H Cl Cl F Cl t-Bu H Cl Cl Br Cl t-Bu H Cl Cl F Cl Me Me Cl ClBr Cl Me Me Br Cl F Cl Me H Br Cl Br Cl Me H Br Cl F Cl Et H Br Cl Br ClEt H Br Cl F Cl i-Pr H Br Cl Br Cl i-Pr H Br Cl F Cl t-Bu H Br Cl Br Clt-Bu H Br Cl F Cl Me Me Br Cl Br Cl Me Me Cl Br F Cl Me H Cl Br Br Cl MeH Cl Br F Cl Et H Cl Br Br Cl Et H Cl Br F Cl i-Pr H Cl Br Br Cl i-Pr HCl Br F Cl t-Bu H Cl Br Br Cl t-Bu H Cl Br F Cl Me Me Cl Br Br Cl Me MeBr Br F Cl Me H Br Br Br Cl Me H Br Br F Cl Et H Br Br Br Cl Et H Br BrF Cl i-Pr H Br Br Br Cl i-Pr H Br Br F Cl t-Bu H Br Br Br Cl t-Bu H BrBr F Cl Me Me Br Br Br Cl Me Me Cl OCH₂CF₃ F Cl Me H Cl OCH₂CF₃ Br Cl MeH Cl OCH₂CF₃ F Cl Et H Cl OCH₂CF₃ Br Cl Et H Cl OCH₂CF₃ F Cl i-Pr H ClOCH₂CF₃ Br Cl i-Pr H Cl OCH₂CF₃ F Cl t-Bu H Cl OCH₂CF₃ Br Cl t-Bu H ClOCH₂CF₃ F Cl Me Me Cl OCH₂CF₃ Br Cl Me Me Br OCH₂CF₃ F Cl Me H BrOCH₂CF₃ Br Cl Me H Br OCH₂CF₃ F Cl Et H Br OCH₂CF₃ Br Cl Et H Br OCH₂CF₃F Cl i-Pr H Br OCH₂CF₃ Br Cl i-Pr H Br OCH₂CF₃ F Cl t-Bu H Br OCH₂CF₃ BrCl t-Bu H Br OCH₂CF₃ F Cl Me Me Br OCH₂CF₃ Br Cl Me Me Cl CF₃ F Br Me HCl CF₃ Br Br Me H Cl CF₃ F Br Et H Cl CF₃ Br Br Et H Cl CF₃ F Br i-Pr HCl CF₃ Br Br i-Pr H Cl CF₃ F Br t-Bu H Cl CF₃ Br Br t-Bu H Cl CF₃ F BrMe Me Cl CF₃ Br Br Me Me Br CF₃ F Br Me H Br CF₃ Br Br Me H Br CF₃ F BrEt H Br CF₃ Br Br Et H Br CF₃ F Br i-Pr H Br CF₃ Br Br i-Pr H Br CF₃ FBr t-Bu H Br CF₃ Br Br t-Bu H Br CF₃ F Br Me Me Br CF₃ Br Br Me Me Cl ClF Br Me H Cl Cl Br Br Me H Cl Cl F Br Et H Cl Cl Br Br Et H Cl Cl F Bri-Pr H Cl Cl Br Br i-Pr H Cl Cl F Br t-Bu H Cl Cl Br Br t-Bu H Cl Cl FBr Me Me Cl Cl Br Br Me Me Br Cl F Br Me H Br Cl Br Br Me H Br Cl F BrEt H Br Cl Br Br Et H Br Cl F Br i-Pr H Br Cl Br Br i-Pr H Br Cl F Brt-Bu H Br Cl Br Br t-Bu H Br Cl F Br Me Me Br Cl Br Br Me Me Cl Br F BrMe H Cl Br Br Br Me H Cl Br F Br Et H Cl Br Br Br Et H Cl Br F Br i-Pr HCl Br Br Br i-Pr H Cl Br F Br t-Bu H Cl Br Br Br t-Bu H Cl Br F Br Me MeCl Br Br Br Me Me Br Br F Br Me H Br Br Br Br Me H Br Br F Br Et H Br BrBr Br Et H Br Br F Br i-Pr H Br Br Br Br i-Pr H Br Br F Br t-Bu H Br BrBr Br t-Bu H Br Br F Br Me Me Br Br Br Br Me Me Cl OCH₂CF₃ F Br Me H ClOCH₂CF₃ Br Br Me H Cl OCH₂CF₃ F Br Et H Cl OCH₂CF₃ Br Br Et H Cl OCH₂CF₃F Br i-Pr H Cl OCH₂CF₃ Br Br i-Pr H Cl OCH₂CF₃ F Br t-Bu H Cl OCH₂CF₃ BrBr t-Bu H Cl OCH₂CF₃ F Br Me Me Cl OCH₂CF₃ Br Br Me Me Br OCH₂CF₃ F BrMe H Br OCH₂CF₃ Br Br Me H Br OCH₂CF₃ F Br Et H Br OCH₂CF₃ Br Br Et H BrOCH₂CF₃ F Br i-Pr H Br OCH₂CF₃ Br Br i-Pr H Br OCH₂CF₃ F Br t-Bu H BrOCH₂CF₃ Br Br t-Bu H Br OCH₂CF₃ F Br Me Me Br OCH₂CF₃ Br Br Me Me Cl CF₃F I Me H Cl CF₃ Br I Me H Cl CF₃ F I Et H Cl CF₃ Br I Et H Cl CF₃ F Ii-Pr H Cl CF₃ Br I i-Pr H Cl CF₃ F I t-Bu H Cl CF₃ Br I t-Bu H Cl CF₃ FI Me Me Cl CF₃ Br I Me Me Br CF₃ F I Me H Br CF₃ Br I Me H Br CF₃ F I EtH Br CF₃ Br I Et H Br CF₃ F I i-Pr H Br CF₃ Br I i-Pr H Br CF₃ F I t-BuH Br CF₃ Br I t-Bu H Br CF₃ F I Me Me Br CF₃ Br I Me Me Cl Cl F I Me HCl Cl Br I Me H Cl Cl F I Et H Cl Cl Br I Et H Cl Cl F I i-Pr H Cl Cl BrI i-Pr H Cl Cl F I t-Bu H Cl Cl Br I t-Bu H Cl Cl F I Me Me Cl Cl Br IMe Me Br Cl F I Me H Br Cl Br I Me H Br Cl F I Et H Br Cl Br I Et H BrCl F I i-Pr H Br Cl Br I i-Pr H Br Cl F I t-Bu H Br Cl Br I t-Bu H Br ClF I Me Me Br Cl Br I Me Me Cl Br F I Me H Cl Br Br I Me H Cl Br F I Et HCl Br Br I Et H Cl Br F I i-Pr H Cl Br Br I i-Pr H Cl Br F I t-Bu H ClBr Br I t-Bu H Cl Br F I Me Me Cl Br Br I Me Me Br Br F I Me H Br Br BrI Me H Br Br F I Et H Br Br Br I Et H Br Br F I i-Pr H Br Br Br I i-Pr HBr Br F I t-Bu H Br Br Br I t-Bu H Br Br F I Me Me Br Br Br I Me Me ClOCH₂CF₃ F I Me H Cl OCH₂CF₃ Br I Me H Cl OCH₂CF₃ F I Et H Cl OCH₂CF₃ BrI Et H Cl OCH₂CF₃ F I I-Pr H Cl OCH₂CF₃ Br I i-Pr H Cl OCH₂CF₃ F I t-BuH Cl OCH₂CF₃ Br I t-Bu H Cl OCH₂CF₃ F I Me Me Cl OCH₂CF₃ Br I Me Me BrOCH₂CF₃ F I Me H Br OCH₂CF₃ Br I Me H Br OCH₂CF₃ F I Et H Br OCH₂CF₃ BrI Et H Br OCH₂CF₃ F I i-Pr H Br OCH₂CF₃ Br I i-Pr H Br OCH₂CF₃ F I t-BuH Br OCH₂CF₃ Br I t-Bu H Br OCH₂CF₃ F I Me Me Br OCH₂CF₃ Br I Me Me ClCF₃ F CF₃ Me H Cl CF₃ Br CF₃ Me H Cl CF₃ F CF₃ Et H Cl CF₃ Br CF₃ Et HCl CF₃ F CF₃ i-Pr H Cl CF₃ Br CF₃ i-Pr H Cl CF₃ F CF₃ t-Bu H Cl CF₃ BrCF₃ t-Bu H Cl CF₃ F CF₃ Me Me Cl CF₃ Br CF₃ Me Me Br CF₃ F CF₃ Me H BrCF₃ Br CF₃ Me H Br CF₃ F CF₃ Et H Br CF₃ Br CF₃ Et H Br CF₃ F CF₃ i-Pr HBr CF₃ Br CF₃ i-Pr H Br CF₃ F CF₃ t-Bu H Br CF₃ Br CF₃ t-Bu H Br CF₃ FCF₃ Me Me Br CF₃ Br CF₃ Me Me Cl Cl F CF₃ Me H Cl Cl Br CF₃ Me H Cl Cl FCF₃ Et H Cl Cl Br CF₃ Et H Cl Cl F CF₃ i-Pr H Cl Cl Br CF₃ i-Pr H Cl ClF CF₃ t-Bu H Cl Cl Br CF₃ t-Bu H Cl Cl F CF₃ Me Me Cl Cl Br CF₃ Me Me BrCl F CF₃ Me H Br Cl Br CF₃ Me H Br Cl F CF₃ Et H Br Cl Br CF₃ Et H Br ClF CF₃ i-Pr H Br Cl Br CF₃ i-Pr H Br Cl F CF₃ t-Bu H Br Cl Br CF₃ t-Bu HBr Cl F CF₃ Me Me Br Cl Br CF₃ Me Me Cl Br F CF₃ Me H Cl Br Br CF₃ Me HCl Br F CF₃ Et H Cl Br Br CF₃ Et H Cl Br F CF₃ i-Pr H Cl Br Br CF₃ i-PrH Cl Br F CF₃ t-Bu H Cl Br Br CF₃ t-Bu H Cl Br F CF₃ Me Me Cl Br Br CF₃Me Me Br Br F CF₃ Me H Br Br Br CF₃ Me H Br Br F CF₃ Et H Br Br Br CF₃Et H Br Br F CF₃ i-Pr H Br Br Br CF₃ i-Pr H Br Br F CF₃ t-Bu H Br Br BrCF₃ t-Bu H Br Br F CF₃ Me Me Br Br Br CF₃ Me Me Cl OCH₂CF₃ F CF₃ Me H ClOCH₂CF₃ Br CF₃ Me H Cl OCH₂CF₃ F CF₃ Et H Cl OCH₂CF₃ Br CF₃ Et H ClOCH₂CF₃ F CF₃ i-Pr H Cl OCH₂CF₃ Br CF₃ i-Pr H Cl OCH₂CF₃ F CF₃ t-Bu H ClOCH₂CF₃ Br CF₃ t-Bu H Cl OCH₂CF₃ F CF₃ Me Me Cl OCH₂CF₃ Br CF₃ Me Me BrOCH₂CF₃ F CF₃ Me H Br OCH₂CF₃ Br CF₃ Me H Br OCH₂CF₃ F CF₃ Et H BrOCH₂CF₃ Br CF₃ Et H Br OCH₂CF₃ F CF₃ i-Pr H Br OCH₂CF₃ Br CF₃ i-Pr H BrOCH₂CF₃ F CF₃ t-Bu H Br OCH₂CF₃ Br CF₃ t-Bu H Br OCH₂CF₃ F CF₃ Me Me BrOCH₂CF₃ Br CF₃ Me Me

[0255] TABLE 3

R⁶(a) R⁵(a) R⁴(a) R⁴(b) R³ R² Cl CF₃ CH₃ H Me H Cl CF₃ CH₃ H Et H Cl CF₃CH₃ H i-Pr H Cl CF₃ CH₃ H t-Bu H Cl CF₃ CH₃ H Me Me Br CF₃ CH₃ H Me H BrCF₃ CH₃ H Et H Br CF₃ CH₃ H i-Pr H Br CF₃ CH₃ H t-Bu H Br CF₃ CH₃ H MeMe Cl Cl CH₃ H Me H Cl Cl CH₃ H Et H Cl Cl CH₃ H i-Pr H Cl Cl CH₃ H t-BuH Cl Cl CH₃ H Me Me Br Cl CH₃ H Me H Br Cl CH₃ H Et H Br Cl CH₃ H i-Pr HBr Cl CH₃ H t-Bu H Br Cl CH₃ H Me Me Cl Br CH₃ H Me H Cl Br CH₃ H Et HCl Br CH₃ H i-Pr H Cl Br CH₃ H t-Bu H Cl Br CH₃ H Me Me Br Br CH₃ H Me HBr Br CH₃ H Et H Br Br CH₃ H i-Pr H Br Br CH₃ H t-Bu H Br Br CH₃ H Me MeCl OCH₂CF₃ CH₃ H Me H Cl OCH₂CF₃ CH₃ H Et H Cl OCH₂CF₃ CH₃ H i-Pr H ClOCH₂CF₃ CH₃ H t-Bu H Cl OCH₂CF₃ CH₃ H Me Me Br OCH₂CF₃ CH₃ H Me H BrOCH₂CF₃ CH₃ H Et H Br OCH₂CF₃ CH₃ H i-Pr H Br OCH₂CF₃ CH₃ H t-Bu H BrOCH₂CF₃ CH₃ H Me Me Cl CF₃ CH₃ F Me H Cl CF₃ CH₃ F Et H Cl CF₃ CH₃ Fi-Pr H Cl CF₃ CH₃ F t-Bu H Cl CF₃ CH₃ F Me Me Br CF₃ CH₃ F Me H Br CF₃CH₃ F Et H Br CF₃ CH₃ F i-Pr H Br CF₃ CH₃ F t-Bu H Br CF₃ CH₃ F Me Me ClCl CH₃ F Me H Cl Cl CH₃ F Et H Cl Cl CH₃ F i-Pr H Cl Cl CH₃ F t-Bu H ClCl CH₃ F Me Me Br Cl CH₃ F Me H Br Cl CH₃ F Et H Br Cl CH₃ F i-Pr H BrCl CH₃ F t-Bu H Br Cl CH₃ F Me Me Cl Br CH₃ F Me H Cl Br CH₃ F Et H ClBr CH₃ F i-Pr H Cl Br CH₃ F t-Bu H Cl Br CH₃ F Me Me Br Br CH₃ F Me H BrBr CH₃ F Et H Br Br CH₃ F i-Pr H Br Br CH₃ F t-Bu H Br Br CH₃ F Me Me ClOCH₂CF₃ CH₃ F Me H Cl OCH₂CF₃ CH₃ F Et H Cl OCH₂CF₃ CH₃ F i-Pr H ClOCH₂CF₃ CH₃ F t-Bu H Cl OCH₂CF₃ CH₃ F Me Me Br OCH₂CF₃ CH₃ F Me H BrOCH₂CF₃ CH₃ F Et H Br OCH₂CF₃ CH₃ F i-Pr H Br OCH₂CF₃ CH₃ F t-Bu H BrOCH₂CF₃ CH₃ F Me Me Cl CF₃ CH₃ Cl Me H Cl CF₃ CH₃ Cl Et H Cl CF₃ CH₃ Cli-Pr H Cl CF₃ CH₃ Cl t-Bu H Cl CF₃ CH₃ Cl Me Me Br CF₃ CH₃ Cl Me H BrCF₃ CH₃ Cl Et H Br CF₃ CH₃ Cl i-Pr H Br CF₃ CH₃ Cl t-Bu H Br CF₃ CH₃ ClMe Me Cl Cl CH₃ Cl Me H Cl Cl CH₃ Cl Et H Cl Cl CH₃ Cl i-Pr H Cl Cl CH₃Cl t-Bu H Cl Cl CH₃ Cl Me Me Br Cl CH₃ Cl Me H Br Cl CH₃ Cl Et H Br ClCH₃ Cl i-Pr H Br Cl CH₃ Cl t-Bu H Br Cl CH₃ Cl Me Me Cl Br CH₃ Cl Me HCl Br CH₃ Cl Et H Cl Br CH₃ Cl i-Pr H Cl Br CH₃ Cl t-Bu H Cl Br CH₃ ClMe Me Br Br CH₃ Cl Me H Br Br CH₃ Cl Et H Br Br CH₃ Cl i-Pr H Br Br CH₃Cl t-Bu H Br Br CH₃ Cl Me Me Cl OCH₂CF₃ CH₃ Cl Me H Cl OCH₂CF₃ CH₃ Cl EtH Cl OCH₂CF₃ CH₃ Cl i-Pr H Cl OCH₂CF₃ CH₃ Cl t-Bu H Cl OCH₂CF₃ CH₃ Cl MeMe Br OCH₂CF₃ CH₃ Cl Me H Br OCH₂CF₃ CH₃ Cl Et H Br OCH₂CF₃ CH₃ Cl i-PrH Br OCH₂CF₃ CH₃ Cl t-Bu H Br OCH₂CF₃ CH₃ Cl Me Me Cl CF₃ CH₃ Br Me H ClCF₃ CH₃ Br Et H Cl CF₃ CH₃ Br i-Pr H Cl CF₃ CH₃ Br t-Bu H Cl CF₃ CH₃ BrMe Me Br CF₃ CH₃ Br Me H Br CF₃ CH₃ Br Et H Br CF₃ CH₃ Br i-Pr H Br CF₃CH₃ Br t-Bu H Br CF₃ CH₃ Br Me Me Cl Cl CH₃ Br Me H Cl Cl CH₃ Br Et H ClCl CH₃ Br i-Pr H Cl Cl CH₃ Br t-Bu H Cl Cl CH₃ Br Me Me Br Cl CH₃ Br MeH Br Cl CH₃ Br Et H Br Cl CH₃ Br i-Pr H Br Cl CH₃ Br t-Bu H Br Cl CH₃ BrMe Me Cl Br CH₃ Br Me H Cl Br CH₃ Br Et H Cl Br CH₃ Br i-Pr H Cl Br CH₃Br t-Bu H Cl Br CH₃ Br Me Me Br Br CH₃ Br Me H Br Br CH₃ Br Et H Br BrCH₃ Br i-Pr H Br Br CH₃ Br t-Bu H Br Br CH₃ Br Me Me Cl OCH₂CF₃ CH₃ BrMe H Cl OCH₂CF₃ CH₃ Br Et H Cl OCH₂CF₃ CH₃ Br i-Pr H Cl OCH₂CF₃ CH₃ Brt-Bu H Cl OCH₂CF₃ CH₃ Br Me Me Br OCH₂CF₃ CH₃ Br Me H Br OCH₂CF₃ CH₃ BrEt H Br OCH₂CF₃ CH₃ Br i-Pr H Br OCH₂CF₃ CH₃ Br t-Bu H Br OCH₂CF₃ CH₃ BrMe Me Cl CF₃ CH₃ I Me H Cl CF₃ CH₃ I Et H Cl CF₃ CH₃ I i-Pr H Cl CF₃ CH₃I t-Bu H Cl CF₃ CH₃ I Me Me Br CF₃ CH₃ I Me H Br CF₃ CH₃ I Et H Br CF₃CH₃ I i-Pr H Br CF₃ CH₃ I t-Bu H Br CF₃ CH₃ I Me Me Cl Cl CH₃ I Me H ClCl CH₃ I Et H Cl Cl CH₃ I i-Pr H Cl Cl CH₃ I t-Bu H Cl Cl CH₃ I Me Me BrCl CH₃ I Me H Br Cl CH₃ I Et H Br Cl CH₃ I i-Pr H Br Cl CH₃ I t-Bu H BrCl CH₃ I Me Me Cl Br CH₃ I Me H Cl Br CH₃ I Et H Cl Br CH₃ I i-Pr H ClBr CH₃ I t-Bu H Cl Br CH₃ I Me Me Br Br CH₃ I Me H Br Br CH₃ I Et H BrBr CH₃ I i-Pr H Br Br CH₃ I t-Bu H Br Br CH₃ I Me Me Cl OCH₂CF₃ CH₃ I MeH Cl OCH₂CF₃ CH₃ I Et H Cl OCH₂CF₃ CH₃ I i-Pr H Cl OCH₂CF₃ CH₃ I t-Bu HCl OCH₂CF₃ CH₃ I Me Me Br OCH₂CF₃ CH₃ I Me H Br OCH₂CF₃ CH₃ I Et H BrOCH₂CF₃ CH₃ I i-Pr H Br OCH₂CF₃ CH₃ I t-Bu H Br OCH₂CF₃ CH₃ I Me Me ClCF₃ CH₃ CF₃ Me H Cl CF₃ CH₃ CF₃ Et H Cl CF₃ CH₃ CF₃ i-Pr H Cl CF₃ CH₃CF₃ t-Bu H Cl CF₃ CH₃ CF₃ Me Me Br CF₃ CH₃ CF₃ Me H Br CF₃ CH₃ CF₃ Et HBr CF₃ CH₃ CF₃ i-Pr H Br CF₃ CH₃ CF₃ t-Bu H Br CF₃ CH₃ CF₃ Me Me Cl ClCH₃ CF₃ Me H Cl Cl CH₃ CF₃ Et H Cl Cl CH₃ CF₃ i-Pr H Cl Cl CH₃ CF₃ t-BuH Cl Cl CH₃ CF₃ Me Me Br Cl CH₃ CF₃ Me H Br Cl CH₃ CF₃ Et H Br Cl CH₃CF₃ i-Pr H Br Cl CH₃ CF₃ t-Bu H Br Cl CH₃ CF₃ Me Me Cl Br CH₃ CF₃ Me HCl Br CH₃ CF₃ Et H Cl Br CH₃ CF₃ i-Pr H Cl Br CH₃ CF₃ t-Bu H Cl Br CH₃CF₃ Me Me Br Br CH₃ CF₃ Me H Br Br CH₃ CF₃ Et H Br Br CH₃ CF₃ i-Pr H BrBr CH₃ CF₃ t-Bu H Br Br CH₃ CF₃ Me Me Cl OCH₂CF₃ CH₃ CF₃ Me H Cl OCH₂CF₃CH₃ CF₃ Et H Cl OCH₂CF₃ CH₃ CF₃ i-Pr H Cl OCH₂CF₃ CH₃ CF₃ t-Bu H ClOCH₂CF₃ CH₃ CF₃ Me Me Br OCH₂CF₃ CH₃ CF₃ Me H Br OCH₂CF₃ CH₃ CF₃ Et H BrOCH₂CF₃ CH₃ CF₃ i-Pr H Br OCH₂CF₃ CH₃ CF₃ t-Bu H Br OCH₂CF₃ CH₃ CF₃ MeMe Cl Cl CH₃ Cl n-Pr H Cl Cl CH₃ Cl n-Bu H Cl Cl CH₃ Cl s-Bu H Cl Cl CH₃Cl i-Bu H Cl Cl CH₃ Cl Et Me Cl CF₃ F H Me H Cl CF₃ F H Et H Cl CF₃ F Hi-Pr H Cl CF₃ F H t-Bu H Cl CF₃ F H Me Me Br CF₃ F H Me H Br CF₃ F H EtH Br CF₃ F H i-Pr H Br CF₃ F H t-Bu H Br CF₃ F H Me Me Cl Cl F H Me H ClCl F H Et H Cl Cl F H i-Pr H Cl Cl F H t-Bu H Cl Cl F H Me Me Br Cl F HMe H Br Cl F H Et H Br Cl F H i-Pr H Br Cl F H t-Bu H Br Cl F H Me Me ClBr F H Me H Cl Br F H Et H Cl Br F H i-Pr H Cl Br F H t-Bu H Cl Br F HMe Me Br Br F H Me H Br Br F H Et H Br Br F H i-Pr H Br Br F H t-Bu H BrBr F H Me Me Cl OCH₂CF₃ F H Me H Cl OCH₂CF₃ F H Et H Cl OCH₂CF₃ F H i-PrH Cl OCH₂CF₃ F H t-Bu H Cl OCH₂CF₃ F H Me Me Br OCH₂CF₃ F H Me H BrOCH₂CF₃ F H Et H Br OCH₂CF₃ F H i-Pr H Br OCH₂CF₃ F H t-Bu H Br OCH₂CF₃F H Me Me Cl CF₃ F F Me H Cl CF₃ F F Et H Cl CF₃ F F i-Pr H Cl CF₃ F Ft-Bu H Cl CF₃ F F Me Me Br CF₃ F F Me H Br CF₃ F F Et H Br CF₃ F F i-PrH Br CF₃ F F t-Bu H Br CF₃ F F Me Me Cl Cl F F Me H Cl Cl F F Et H Cl ClF F i-Pr H Cl Cl F F t-Bu H Cl Cl F F Me Me Br Cl F F Me H Br Cl F F EtH Br Cl F F i-Pr H Br Cl F F t-Bu H Br Cl F F Me Me Cl Br F F Me H Cl BrF F Et H Cl Br F F i-Pr H Cl Br F F t-Bu H Cl Br F F Me Me Br Br F F MeH Br Br F F Et H Br Br F F i-Pr H Br Br F F t-Bu H Br Br F F Me Me ClOCH₂CF₃ F F Me H Cl OCH₂CF₃ F F Et H Cl OCH₂CF₃ F F i-Pr H Cl OCH₂CF₃ FF t-Bu H Cl OCH₂CF₃ F F Me Me Br OCH₂CF₃ F F Me H Br OCH₂CF₃ F F Et H BrOCH₂CF₃ F F i-Pr H Br OCH₂CF₃ F F t-Bu H Br OCH₂CF₃ F F Me Me Cl CF₃ FCl Me H Cl CF₃ F Cl Et H Cl CF₃ F Cl i-Pr H Cl CF₃ F Cl t-Bu H Cl CF₃ FCl Me Me Br CF₃ F Cl Me H Br CF₃ F Cl Et H Br CF₃ F Cl i-Pr H Br CF₃ FCl t-Bu H Br CF₃ F Cl Me Me Cl Cl F Cl Me H Cl Cl F Cl Et H Cl Cl F Cli-Pr H Cl Cl F Cl t-Bu H Cl Cl F Cl Me Me Br Cl F Cl Me H Br Cl F Cl EtH Br Cl F Cl i-Pr H Br Cl F Cl t-Bu H Br Cl F Cl Me Me Cl Br F Cl Me HCl Br F Cl Et H Cl Br F Cl i-Pr H Cl Br F Cl t-Bu H Cl Br F Cl Me Me BrBr F Cl Me H Br Br F Cl Et H Br Br F Cl i-Pr H Br Br F Cl t-Bu H Br Br FCl Me Me Cl OCH₂CF₃ F Cl Me H Cl OCH₂CF₃ F Cl Et H Cl OCH₂CF₃ F Cl i-PrH Cl OCH₂CF₃ F Cl t-Bu H Cl OCH₂CF₃ F Cl Me Me Br OCH₂CF₃ F Cl Me H BrOCH₂CF₃ F Cl Et H Br OCH₂CF₃ F Cl i-Pr H Br OCH₂CF₃ F Cl t-Bu H BrOCH₂CF₃ F Cl Me Me Cl CF₃ F Br Me H Cl CF₃ F Br Et H Cl CF₃ F Br i-Pr HCl CF₃ F Br t-Bu H Cl CF₃ F Br Me Me Br CF₃ F Br Me H Br CF₃ F Br Et HBr CF₃ F Br i-Pr H Br CF₃ F Br t-Bu H Br CF₃ F Br Me Me Cl Cl F Br Me HCl Cl F Br Et H Cl Cl F Br i-Pr H Cl Cl F Br t-Bu H Cl Cl F Br Me Me BrCl F Br Me H Br Cl F Br Et H Br Cl F Br i-Pr H Br Cl F Br t-Bu H Br Cl FBr Me Me Cl Br F Br Me H Cl Br F Br Et H Cl Br F Br i-Pr H Cl Br F Brt-Bu H Cl Br F Br Me Me Br Br F Br Me H Br Br F Br Et H Br Br F Br i-PrH Br Br F Br t-Bu H Br Br F Br Me Me Cl OCH₂CF₃ F Br Me H Cl OCH₂CF₃ FBr Et H Cl OCH₂CF₃ F Br i-Pr H Cl OCH₂CF₃ F Br t-Bu H Cl OCH₂CF₃ F Br MeMe Br OCH₂CF₃ F Br Me H Br OCH₂CF₃ F Br Et H Br OCH₂CF₃ F Br i-Pr H BrOCH₂CF₃ F Br t-Bu H Br OCH₂CF₃ F Br Me Me Cl CF₃ F I Me H Cl CF₃ F I EtH Cl CF₃ F I i-Pr H Cl CF₃ F I t-Bu H Cl CF₃ F I Me Me Br CF₃ F I Me HBr CF₃ F I Et H Br CF₃ F I i-Pr H Br CF₃ F I t-Bu H Br CF₃ F I Me Me ClCl F I Me H Cl Cl F I Et H Cl Cl F I i-Pr H Cl Cl F I t-Bu H Cl Cl F IMe Me Br Cl F I Me H Br Cl F I Et H Br Cl F I i-Pr H Br Cl F I t-Bu H BrCl F I Me Me Cl Br F I Me H Cl Br F I Et H Cl Br F I i-Pr H Cl Br F It-Bu H Cl Br F I Me Me Br Br F I Me H Br Br F I Et H Br Br F I i-Pr H BrBr F I t-Bu H Br Br F I Me Me Cl OCH₂CF₃ F I Me H Cl OCH₂CF₃ F I Et H ClOCH₂CF₃ F I i-Pr H Cl OCH₂CF₃ F I t-Bu H Cl OCH₂CF₃ F I Me Me Br OCH₂CF₃F I Me H Br OCH₂CF₃ F I Et H Br OCH₂CF₃ F I i-Pr H Br OCH₂CF₃ F I t-Bu HBr OCH₂CF₃ F I Me Me Cl CF₃ F CF₃ Me H Cl CF₃ F CF₃ Et H Cl CF₃ F CF₃i-Pr H Cl CF₃ F CF₃ t-Bu H Cl CF₃ F CF₃ Me Me Br CF₃ F CF₃ Me H Br CF₃ FCF₃ Et H Br CF₃ F CF₃ i-Pr H Br CF₃ F CF₃ t-Bu H Br CF₃ F CF₃ Me Me ClCl F CF₃ Me H Cl Cl F CF₃ Et H Cl Cl F CF₃ i-Pr H Cl Cl F CF₃ t-Bu H ClCl F CF₃ Me Me Br Cl F CF₃ Me H Br Cl F CF₃ Et H Br Cl F CF₃ i-Pr H BrCl F CF₃ t-Bu H Br Cl F CF₃ Me Me Cl Br F CF₃ Me H Cl Br F CF₃ Et H ClBr F CF₃ i-Pr H Cl Br F CF₃ t-Bu H Cl Br F CF₃ Me Me Br Br F CF₃ Me H BrBr F CF₃ Et H Br Br F CF₃ i-Pr H Br Br F CF₃ t-Bu H Br Br F CF₃ Me Me ClOCH₂CF₃ F CF₃ Me H Cl OCH₂CF₃ F CF₃ Et H Cl OCH₂CF₃ F CF₃ i-Pr H ClOCH₂CF₃ F CF₃ t-Bu H Cl OCH₂CF₃ F CF₃ Me Me Br OCH₂CF₃ F CF₃ Me H BrOCH₂CF₃ F CF₃ Et H Br OCH₂CF₃ F CF₃ i-Pr H Br OCH₂CF₃ F CF₃ t-Bu H BrOCH₂CF₃ F CF₃ Me Me Cl CF₃ Cl H Me H Cl CF₃ Cl H Et H Cl CF₃ Cl H i-Pr HCl CF₃ Cl H t-Bu H Cl CF₃ Cl H Me Me Br CF₃ Cl H Me H Br CF₃ Cl H Et HBr CF₃ Cl H i-Pr H Br CF₃ Cl H t-Bu H Br CF₃ Cl H Me Me Cl Cl Cl H Me HCl Cl Cl H Et H Cl Cl Cl H i-Pr H Cl Cl Cl H t-Bu H Cl Cl Cl H Me Me BrCl Cl H Me H Br Cl Cl H Et H Br Cl Cl H i-Pr H Br Cl Cl H t-Bu H Br ClCl H Me Me Cl Br Cl H Me H Cl Br Cl H Et H Cl Br Cl H i-Pr H Cl Br Cl Ht-Bu H Cl Br Cl H Me Me Br Br Cl H Me H Br Br Cl H Et H Br Br Cl H i-PrH Br Br Cl H t-Bu H Br Br Cl H Me Me Cl OCH₂CF₃ Cl H Me H Cl OCH₂CF₃ ClH Et H Cl OCH₂CF₃ Cl H i-Pr H Cl OCH₂CF₃ Cl H t-Bu H Cl OCH₂CF₃ Cl H MeMe Br OCH₂CF₃ Cl H Me H Br OCH₂CF₃ Cl H Et H Br OCH₂CF₃ Cl H i-Pr H BrOCH₂CF₃ Cl H t-Bu H Br OCH₂CF₃ Cl H Me Me Cl CF₃ Cl F Me H Cl CF₃ Cl FEt H Cl CF₃ Cl F i-Pr H Cl CF₃ Cl F t-Bu H Cl CF₃ Cl F Me Me Br CF₃ Cl FMe H Br CF₃ Cl F Et H Br CF₃ Cl F i-Pr H Br CF₃ Cl F t-Bu H Br CF₃ Cl FMe Me Cl Cl Cl F Me H Cl Cl Cl F Et H Cl Cl Cl F i-Pr H Cl Cl Cl F t-BuH Cl Cl Cl F Me Me Br Cl Cl F Me H Br Cl Cl F Et H Br Cl Cl F i-Pr H BrCl Cl F t-Bu H Br Cl Cl F Me Me Cl Br Cl F Me H Cl Br Cl F Et H Cl Br ClF i-Pr H Cl Br Cl F t-Bu H Cl Br Cl F Me Me Br Br Cl F Me H Br Br Cl FEt H Br Br Cl F i-Pr H Br Br Cl F t-Bu H Br Br Cl F Me Me Cl OCH₂CF₃ ClF Me H Cl OCH₂CF₃ Cl F Et H Cl OCH₂CF₃ Cl F i-Pr H Cl OCH₂CF₃ Cl F t-BuH Cl OCH₂CF₃ Cl F Me Me Br OCH₂CF₃ Cl F Me H Br OCH₂CF₃ Cl F Et H BrOCH₂CF₃ Cl F i-Pr H Br OCH₂CF₃ Cl F t-Bu H Br OCH₂CF₃ Cl F Me Me Cl CF₃Cl Cl Me H Cl CF₃ Cl Cl Et H Cl CF₃ Cl Cl i-Pr H Cl CF₃ Cl Cl t-Bu H ClCF₃ Cl Cl Me Me Br CF₃ Cl Cl Me H Br CF₃ Cl Cl Et H Br CF₃ Cl Cl i-Pr HBr CF₃ Cl Cl t-Bu H Br CF₃ Cl Cl Me Me Cl Cl Cl Cl Me H Cl Cl Cl Cl Et HCl Cl Cl Cl i-Pr H Cl Cl Cl Cl t-Bu H Cl Cl Cl Cl Me Me Br Cl Cl Cl Me HBr Cl Cl Cl Et H Br Cl Cl Cl i-Pr H Br Cl Cl Cl t-Bu H Br Cl Cl Cl Me MeCl Br Cl Cl Me H Cl Br Cl Cl Et H Cl Br Cl Cl i-Pr H Cl Br Cl Cl t-Bu HCl Br Cl Cl Me Me Br Br Cl Cl Me H Br Br Cl Cl Et H Br Br Cl Cl i-Pr HBr Br Cl Cl t-Bu H Br Br Cl Cl Me Me Cl OCH₂CF₃ Cl Cl Me H Cl OCH₂CF₃ ClCl Et H Cl OCH₂CF₃ Cl Cl i-Pr H Cl OCH₂CF₃ Cl Cl t-Bu H Cl OCH₂CF₃ Cl ClMe Me Br OCH₂CF₃ Cl Cl Me H Br OCH₂CF₃ Cl Cl Et H Br OCH₂CF₃ Cl Cl i-PrH Br OCH₂CF₃ Cl Cl t-Bu H Br OCH₂CF₃ Cl Cl Me Me Cl CF₃ Cl Br Me H ClCF₃ Cl Br Et H Cl CF₃ Cl Br i-Pr H Cl CF₃ Cl Br t-Bu H Cl CF₃ Cl Br MeMe Br CF₃ Cl Br Me H Br CF₃ Cl Br Et H Br CF₃ Cl Br i-Pr H Br CF₃ Cl Brt-Bu H Br CF₃ Cl Br Me Me Cl Cl Cl Br Me H Cl Cl Cl Br Et H Cl Cl Cl Bri-Pr H Cl Cl Cl Br t-Bu H Cl Cl Cl Br Me Me Br Cl Cl Br Me H Br Cl Cl BrEt H Br Cl Cl Br i-Pr H Br Cl Cl Br t-Bu H Br Cl Cl Br Me Me Cl Br Cl BrMe H Cl Br Cl Br Et H Cl Br Cl Br i-Pr H Cl Br Cl Br t-Bu H Cl Br Cl BrMe Me Br Br Cl Br Me H Br Br Cl Br Et H Br Br Cl Br i-Pr H Br Br Cl Brt-Bu H Br Br Cl Br Me Me Cl OCH₂CF₃ Cl Br Me H Cl OCH₂CF₃ Cl Br Et H ClOCH₂CF₃ Cl Br i-Pr H Cl OCH₂CF₃ Cl Br t-Bu H Cl OCH₂CF₃ Cl Br Me Me BrOCH₂CF₃ Cl Br Me H Br OCH₂CF₃ Cl Br Et H Br OCH₂CF₃ Cl Br i-Pr H BrOCH₂CF₃ Cl Br t-Bu H Br OCH₂CF₃ Cl Br Me Me Cl CF₃ Cl I Me H Cl CF₃ Cl IEt H Cl CF₃ Cl I i-Pr H Cl CF₃ Cl I t-Bu H Cl CF₃ Cl I Me Me Br CF₃ Cl IMe H Br CF₃ Cl I Et H Br CF₃ Cl I i-Pr H Br CF₃ Cl I t-Bu H Br CF₃ Cl IMe Me Cl Cl Cl I Me H Cl Cl Cl I Et H Cl Cl Cl I i-Pr H Cl Cl Cl I t-BuH Cl Cl Cl I Me Me Br Cl Cl I Me H Br Cl Cl I Et H Br Cl Cl I i-Pr H BrCl Cl I t-Bu H Br Cl Cl I Me Me Cl Br Cl I Me H Cl Br Cl I Et H Cl Br ClI i-Pr H Cl Br Cl I t-Bu H Cl Br Cl I Me Me Br Br Cl I Me H Br Br Cl IEt H Br Br Cl I i-Pr H Br Br Cl I t-Bu H Br Br Cl I Me Me Cl OCH₂CF₃ ClI Me H Cl OCH₂CF₃ Cl I Et H Cl OCH₂CF₃ Cl I i-Pr H Cl OCH₂CF₃ Cl I t-BuH Cl OCH₂CF₃ Cl I Me Me Br OCH₂CF₃ Cl I Me H Br OCH₂CF₃ Cl I Et H BrOCH₂CF₃ Cl I i-Pr H Br OCH₂CF₃ Cl I t-Bu H Br OCH₂CF₃ Cl I Me Me Cl CF₃Cl CF₃ Me H Cl CF₃ Cl CF₃ Et H Cl CF₃ Cl CF₃ i-Pr H Cl CF₃ Cl CF₃ t-Bu HCl CF₃ Cl CF₃ Me Me Br CF₃ Cl CF₃ Me H Br CF₃ Cl CF₃ Et H Br CF₃ Cl CF₃i-Pr H Br CF₃ Cl CF₃ t-Bu H Br CF₃ Cl CF₃ Me Me Cl Cl Cl CF₃ Me H Cl ClCl CF₃ Et H Cl Cl Cl CF₃ i-Pr H Cl Cl Cl CF₃ t-Bu H Cl Cl Cl CF₃ Me MeBr Cl Cl CF₃ Me H Br Cl Cl CF₃ Et H Br Cl Cl CF₃ i-Pr H Br Cl Cl CF₃t-Bu H Br Cl Cl CF₃ Me Me Cl Br Cl CF₃ Me H Cl Br Cl CF₃ Et H Cl Br ClCF₃ i-Pr H Cl Br Cl CF₃ t-Bu H Cl Br Cl CF₃ Me Me Br Br Cl CF₃ Me H BrBr Cl CF₃ Et H Br Br Cl CF₃ i-Pr H Br Br Cl CF₃ t-Bu H Br Br Cl CF₃ MeMe Cl OCH₂CF₃ Cl CF₃ Me H Cl OCH₂CF₃ Cl CF₃ Et H Cl OCH₂CF₃ Cl CF₃ i-PrH Cl OCH₂CF₃ Cl CF₃ t-Bu H Cl OCH₂CF₃ Cl CF₃ Me Me Br OCH₂CF₃ Cl CF₃ MeH Br OCH₂CF₃ Cl CF₃ Et H Br OCH₂CF₃ Cl CF₃ i-Pr H Br OCH₂CF₃ Cl CF₃ t-BuH Br OCH₂CF₃ Cl CF₃ Me Me Cl Cl Cl Cl n-Pr H Cl Cl Cl Cl n-Bu H Cl Cl ClCl S-Bu H Cl Cl Cl Cl i-Bu H Cl Cl Cl Cl Et Et Cl CF₃ Br H Me H Cl CF₃Br H Et H Cl CF₃ Br H i-Pr H Cl CF₃ Br H t-Bu H Cl CF₃ Br H Me Me Br CF₃Br H Me H Br CF₃ Br H Et H Br CF₃ Br H i-Pr H Br CF₃ Br H t-Bu H Br CF₃Br H Me Me Cl Cl Br H Me H Cl Cl Br H Et H Cl Cl Br H i-Pr H Cl Cl Br Ht-Bu H Cl Cl Br H Me Me Br Cl Br H Me H Br Cl Br H Et H Br Cl Br H i-PrH Br Cl Br H t-Bu H Br Cl Br H Me Me Cl Br Br H Me H Cl Br Br H Et H ClBr Br H i-Pr H Cl Br Br H t-Bu H Cl Br Br H Me Me Br Br Br H Me H Br BrBr H Et H Br Br Br H i-Pr H Br Br Br H t-Bu H Br Br Br H Me Me Cl OCH₂H₃Br H Me H Cl OCH₂H₃ Br H Et H Cl OCH₂H₃ Br H i-Pr H Cl OCH₂H₃ Br H t-BuH Cl OCH₂H₃ Br H Me Me Br OCH₂H₃ Br H Me H Br OCH₂H₃ Br H Et H Br OCH₂H₃Br H i-Pr H Br OCH₂H₃ Br H t-Bu H Br OCH₂H₃ Br H Me Me Cl CF₃ Br F Me HCl CF₃ Br F Et H Cl CF₃ Br F i-Pr H Cl CF₃ Br F t-Bu H Cl CF₃ Br F Me MeBr CF₃ Br F Me H Br CF₃ Br F Et H Br CF₃ Br F i-Pr H Br CF₃ Br F t-Bu HBr CF₃ Br F Me Me Cl Cl Br F Me H Cl Cl Br F Et H Cl Cl Br F i-Pr H ClCl Br F t-Bu H Cl Cl Br F Me Me Br Cl Br F Me H Br Cl Br F Et H Br Cl BrF i-Pr H Br Cl Br F t-Bu H Br Cl Br F Me Me Cl Br Br F Me H Cl Br Br FEt H Cl Br Br F i-Pr H Cl Br Br F t-Bu H Cl Br Br F Me Me Br Br Br F MeH Br Br Br F Et H Br Br Br F i-Pr H Br Br Br F t-Bu H Br Br Br F Me MeCl OCH₂CF₃ Br F Me H Cl OCH₂CF₃ Br F Et H Cl OCH₂CF₃ Br F i-Pr H ClOCH₂CF₃ Br F t-Bu H Cl OCH₂CF₃ Br F Me Me Br OCH₂CF₃ Br F Me H BrOCH₂CF₃ Br F Et H Br OCH₂CF₃ Br F i-Pr H Br OCH₂CF₃ Br F t-Bu H BrOCH₂CF₃ Br F Me Me Cl CF₃ Br Cl Me H Cl CF₃ Br Cl Et H Cl CF₃ Br Cl i-PrH Cl CF₃ Br Cl t-Bu H Cl CF₃ Br Cl Me Me Br CF₃ Br Cl Me H Br CF₃ Br ClEt H Br CF₃ Br Cl i-Pr H Br CF₃ Br Cl t-Bu H Br CF₃ Br Cl Me Me Cl Cl BrCl Me H Cl Cl Br Cl Et H Cl Cl Br Cl i-Pr H Cl Cl Br Cl t-Bu H Cl Cl BrCl Me Me Br Cl Br Cl Me H Br Cl Br Cl Et H Br Cl Br Cl i-Pr H Br Cl BrCl t-Bu H Br Cl Br Cl Me Me Cl Br Br Cl Me H Cl Br Br Cl Et H Cl Br BrCl i-Pr H Cl Br Br Cl t-Bu H Cl Br Br Cl Me Me Br Br Br Cl Me H Br Br BrCl Et H Br Br Br Cl i-Pr H Br Br Br Cl t-Bu H Br Br Br Cl Me Me ClOCH₂CF₃ Br Cl Me H Cl OCH₂CF₃ Br Cl Et H Cl OCH₂CF₃ Br Cl i-Pr H ClOCH₂CF₃ Br Cl t-Bu H Cl OCH₂CF₃ Br Cl Me Me Br OCH₂CF₃ Br Cl Me H BrOCH₂CF₃ Br Cl Et H Br OCH₂CF₃ Br Cl i-Pr H Br OCH₂CF₃ Br Cl t-Bu H BrOCH₂CF₃ Br Cl Me Me Cl CF₃ Br Br Me H Cl CF₃ Br Br Et H Cl CF₃ Br Bri-Pr H Cl CF₃ Br Br t-Bu H Cl CF₃ Br Br Me Me Br CF₃ Br Br Me H Br CF₃Br Br Et H Br CF₃ Br Br i-Pr H Br CF₃ Br Br t-Bu H Br CF₃ Br Br Me Me ClCl Br Br Me H Cl Cl Br Br Et H Cl Cl Br Br i-Pr H Cl Cl Br Br t-Bu H ClCl Br Br Me Me Br Cl Br Br Me H Br Cl Br Br Et H Br Cl Br Br i-Pr H BrCl Br Br t-Bu H Br Cl Br Br Me Me Cl Br Br Br Me H Cl Br Br Br Et H ClBr Br Br i-Pr H Cl Br Br Br t-Bu H Cl Br Br Br Me Me Br Br Br Br Me H BrBr Br Br Et H Br Br Br Br i-Pr H Br Br Br Br t-Bu H Br Br Br Br Me Me ClOCH₂CF₃ Br Br Me H Cl OCH₂CF₃ Br Br Et H Cl OCH₂CF₃ Br Br i-Pr H ClOCH₂CF₃ Br Br t-Bu H Cl OCH₂CF₃ Br Br Me Me Br OCH₂CF₃ Br Br Me H BrOCH₂CF₃ Br Br Et H Br OCH₂CF₃ Br Br i-Pr H Br OCH₂CF₃ Br Br t-Bu H BrOCH₂CF₃ Br Br Me Me Cl CF₃ Br I Me H Cl CF₃ Br I Et H Cl CF₃ Br I i-Pr HCl CF₃ Br I t-Bu H Cl CF₃ Br I Me Me Br CF₃ Br I Me H Br CF₃ Br I Et HBr CF₃ Br I i-Pr H Br CF₃ Br I t-Bu H Br CF₃ Br I Me Me Cl Cl Br I Me HCl Cl Br I Et H Cl Cl Br I i-Pr H Cl Cl Br I t-Bu H Cl Cl Br I Me Me BrCl Br I Me H Br Cl Br I Et H Br Cl Br I i-Pr H Br Cl Br I t-Bu H Br ClBr I Me Me Cl Br Br I Me H Cl Br Br I Et H Cl Br Br I i-Pr H Cl Br Br It-Bu H Cl Br Br I Me Me Br Br Br I Me H Br Br Br I Et H Br Br Br I i-PrH Br Br Br I t-Bu H Br Br Br I Me Me Cl OCH₂CF₃ Br I Me H Cl OCH₂CF₃ BrI Et H Cl OCH₂CF₃ Br I i-Pr H Cl OCH₂CF₃ Br I t-Bu H Cl OCH₂CF₃ Br I MeMe Br OCH₂CF₃ Br I Me H Br OCH₂CF₃ Br I Et H Br OCH₂CF₃ Br I i-Pr H BrOCH₂CF₃ Br I t-Bu H Br OCH₂CF₃ Br I Me Me Cl CF₃ Br CF₃ Me H Cl CF₃ BrCF₃ Et H Cl CF₃ Br CF₃ i-Pr H Cl CF₃ Br CF₃ t-Bu H Cl CF₃ Br CF₃ Me MeBr CF₃ Br CF₃ Me H Br CF₃ Br CF₃ Et H Br CF₃ Br CF₃ i-Pr H Br CF₃ Br CF₃t-Bu H Br CF₃ Br CF₃ Me Me Cl Cl Br CF₃ Me H Cl Cl Br CF₃ Et H Cl Cl BrCF₃ i-Pr H Cl Cl Br CF₃ t-Bu H Cl Cl Br CF₃ Me Me Br Cl Br CF₃ Me H BrCl Br CF₃ Et H Br Cl Br CF₃ i-Pr H Br Cl Br CF₃ t-Bu H Br Cl Br CF₃ MeMe Cl Br Br CF₃ Me H Cl Br Br CF₃ Et H Cl Br Br CF₃ i-Pr H Cl Br Br CF₃t-Bu H Cl Br Br CF₃ Me Me Br Br Br CF₃ Me H Br Br Br CF₃ Et H Br Br BrCF₃ i-Pr H Br Br Br CF₃ t-Bu H Br Br Br CF₃ Me Me Cl OCH₂CF₃ Br CF₃ Me HCl OCH₂CF₃ Br CF₃ Et H Cl OCH₂CF₃ Br CF₃ i-Pr H Cl OCH₂CF₃ Br CF₃ t-Bu HCl OCH₂CF₃ Br CF₃ Me Me Br OCH₂CF₃ Br CF₃ Me H Br OCH₂CF₃ Br CF₃ Et H BrOCH₂CF₃ Br CF₃ i-Pr H Br OCH₂CF₃ Br CF₃ t-Bu H Br OCH₂CF₃ Br CF₃ Me Me

[0256] TABLE 4

R⁶(a) R⁵(a) R⁴(a) R⁴(b) R³ R² Cl CF₃ CH₃ H Me H Cl CF₃ CH₃ H Et H Cl CF₃CH₃ H i-Pr H Cl CF₃ CH₃ H t-Bu H Cl CF₃ CH₃ H Me Me Br CF₃ CH₃ H Me H BrCF₃ CH₃ H Et H Br CF₃ CH₃ H i-Pr H Br CF₃ CH₃ H t-Bu H Br CF₃ CH₃ H MeMe Cl Cl CH₃ H Me H Cl Cl CH₃ H Et H Cl Cl CH₃ H i-Pr H Cl Cl CH₃ H t-BuH Cl Cl CH₃ H Me Me Br Cl CH₃ H Me H Br Cl CH₃ H Et H Br Cl CH₃ H i-Pr HBr Cl CH₃ H t-Bu H Br Cl CH₃ H Me Me Cl Br CH₃ H Me H Cl Br CH₃ H Et HCl Br CH₃ H i-Pr H Cl Br CH₃ H t-Bu H Cl Br CH₃ H Me Me Br Br CH₃ H Me HBr Br CH₃ H Et H Br Br CH₃ H i-Pr H Br Br CH₃ H t-Bu H Br Br CH₃ H Me MeCl OCH₂CF₃ CH₃ H Me H Cl OCH₂CF₃ CH₃ H Et H Cl OCH₂CF₃ CH₃ H i-Pr H ClOCH₂CF₃ CH₃ H t-Bu H Cl OCH₂CF₃ CH₃ H Me Me Br OCH₂CF₃ CH₃ H Me H BrOCH₂CF₃ CH₃ H Et H Br OCH₂CF₃ CH₃ H i-Pr H Br OCH₂CF₃ CH₃ H t-Bu H BrOCH₂CF₃ CH₃ H Me Me Cl CF₃ CH₃ F Me H Cl CF₃ CH₃ F Et H Cl CF₃ CH₃ Fi-Pr H Cl CF₃ CH₃ F t-Bu H Cl CF₃ CH₃ F Me Me Br CF₃ CH₃ F Me H Br CF₃CH₃ F Et H Br CF₃ CH₃ F i-Pr H Br CF₃ CH₃ F t-Bu H Br CF₃ CH₃ F Me Me ClCl CH₃ F Me H Cl Cl CH₃ F Et H Cl Cl CH₃ F i-Pr H Cl Cl CH₃ F t-Bu H ClCl CH₃ F Me Me Br Cl CH₃ F Me H Br Cl CH₃ F Et H Br Cl CH₃ F i-Pr H BrCl CH₃ F t-Bu H Br Cl CH₃ F Me Me Cl Br CH₃ F Me H Cl Br CH₃ F Et H ClBr CH₃ F i-Pr H Cl Br CH₃ F t-Bu H Cl Br CH₃ F Me Me Br Br CH₃ F Me H BrBr CH₃ F Et H Br Br CH₃ F i-Pr H Br Br CH₃ F t-Bu H Br Br CH₃ F Me Me ClOCH₂CF₃ CH₃ F Me H Cl OCH₂CF₃ CH₃ F Et H Cl OCH₂CF₃ CH₃ F i-Pr H ClOCH₂CF₃ CH₃ F t-Bu H Cl OCH₂CF₃ CH₃ F Me Me Br OCH₂CF₃ CH₃ F Me H BrOCH₂CF₃ CH₃ F Et H Br OCH₂CF₃ CH₃ F i-Pr H Br OCH₂CF₃ CH₃ F t-Bu H BrOCH₂CF₃ CH₃ F Me Me Cl CF₃ CH₃ Cl Me H Cl CF₃ CH₃ Cl Et H Cl CF₃ CH₃ Cli-Pr H Cl CF₃ CH₃ Cl t-Bu H Cl CF₃ CH₃ Cl Me Me Br CF₃ CH₃ Cl Me H BrCF₃ CH₃ Cl Et H Br CF₃ CH₃ Cl i-Pr H Br CF₃ CH₃ Cl t-Bu H Br Cl CH₃ ClMe Me Cl Cl CH₃ Cl Me H Cl Cl CH₃ Cl Et H Cl Cl CH₃ Cl i-Pr H Cl Cl CH₃Cl t-Bu H Cl Cl CH₃ Cl Me Me Br Cl CH₃ Cl Me H Br Cl CH₃ Cl Et H Br ClCH₃ Cl i-Pr H Br Cl CH₃ Cl t-Bu H Br Cl CH₃ Cl Me Me Cl Br CH₃ Cl Me HCl Br CH₃ Cl Et H Cl Br CH₃ Cl i-Pr H Cl Br CH₃ Cl t-Bu H Cl Br CH₃ ClMe Me Br Br CH₃ Cl Me H Br Br CH₃ Cl Et H Br Br CH₃ Cl i-Pr H Br Br CH₃Cl t-Bu H Br Br CH₃ Cl Me Me Cl OCH₂CF₃ CH₃ Cl Me H Cl OCH₂CF₃ CH₃ Cl EtH Cl OCH₂CF₃ CH₃ Cl i-Pr H Cl OCH₂CF₃ CH₃ Cl t-Bu H Cl OCH₂CF₃ CH₃ Cl MeMe Br OCH₂CF₃ CH₃ Cl Me H Br OCH₂CF₃ CH₃ Cl Et H Br OCH₂CF₃ CH₃ Cl i-PrH Br OCH₂CF₃ CH₃ Cl t-Bu H Br OCH₂CF₃ CH₃ Cl Me Me Cl CF₃ CH₃ Br Me H ClCF₃ CH₃ Br Et H Cl CF₃ CH₃ Br i-Pr H Cl CF₃ CH₃ Br t-Bu H Cl CF₃ CH₃ BrMe Me Br CF₃ CH₃ Br Me H Br CF₃ CH₃ Br Et H Br CF₃ CH₃ Br i-Pr H Br CF₃CH₃ Br t-Bu H Br CF₃ CH₃ Br Me Me Cl Cl CH₃ Br Me H Cl Cl CH₃ Br Et H ClCl CH₃ Br i-Pr H Cl Cl CH₃ Br t-Bu H Cl Cl CH₃ Br Me Me Br Cl CH₃ Br MeH Br Cl CH₃ Br Et H Br Cl CH₃ Br i-Pr H Br Cl CH₃ Br t-Bu H Br Cl CH₃ BrMe Me Cl Br CH₃ Br Me H Cl Br CH₃ Br Et H Cl Br CH₃ Br i-Pr H Cl Br CH₃Br t-Bu H Cl Br CH₃ Br Me Me Br Br CH₃ Br Me H Br Br CH₃ Br Et H Br BrCH₃ Br i-Pr H Br Br CH₃ Br t-Bu H Br Br CH₃ Br Me Me Cl OCH₂CF₃ CH₃ BrMe H Cl OCH₂CF₃ CH₃ Br Et H Cl OCH₂CF₃ CH₃ Br i-Pr H Cl OCH₂CF₃ CH₃ Brt-Bu H Cl OCH₂CF₃ CH₃ Br Me Me Br OCH₂CF₃ CH₃ Br Me H Br OCH₂CF₃ CH₃ BrEt H Br OCH₂CF₃ CH₃ Br i-Pr H Br OCH₂CF₃ CH₃ Br t-Bu H Br OCH₂CF₃ CH₃ BrMe Me Cl CF₃ CH₃ I Me H Cl CF₃ CH₃ I Et H Cl CF₃ CH₃ I i-Pr H Cl CF₃ CH₃I t-Bu H Cl CF₃ CH₃ I Me Me Br CF₃ CH₃ I Me H Br CF₃ CH₃ I Et H Br CF₃CH₃ I i-Pr H Br CF₃ CH₃ I t-Bu H Br CF₃ CH₃ I Me Me Cl Cl CH₃ I Me H ClCl CH₃ I Et H Cl Cl CH₃ I i-Pr H Cl Cl CH₃ I t-Bu H Cl Cl CH₃ I Me Me BrCl CH₃ I Me H Br Cl CH₃ I Et H Br Cl CH₃ I i-Pr H Br Cl CH₃ I t-Bu H BrCl CH₃ I Me Me Cl Br CH₃ I Me H Cl Br CH₃ I Et H Cl Br CH₃ I i-Pr H ClBr CH₃ I t-Bu H Cl Br CH₃ I Me Me Br Br CH₃ I Me H Br Br CH₃ I Et H BrBr CH₃ I i-Pr H Br Br CH₃ I t-Bu H Br Br CH₃ I Me Me Cl OCH₂CF₃ CH₃ I MeH Cl OCH₂CF₃ CH₃ I Et H Cl OCH₂CF₃ CH₃ I i-Pr H Cl OCH₂CF₃ CH₃ I t-Bu HCl OCH₂CF₃ CH₃ I Me Me Br OCH₂CF₃ CH₃ I Me H Br OCH₂CF₃ CH₃ I Et H BrOCH₂CF₃ CH₃ I i-Pr H Br OCH₂CF₃ CH₃ I t-Bu H Br OCH₂CF₃ CH₃ I Me Me ClCF₃ CH₃ CF₃ Me H Cl CF₃ CH₃ CF₃ Et H Cl CF₃ CH₃ CF₃ i-Pr H Cl CF₃ CH₃CF₃ t-Bu H Cl CF₃ CH₃ CF₃ Me Me Br CF₃ CH₃ CF₃ Me H Br CF₃ CH₃ CF₃ Et HBr CF₃ CH₃ CF₃ i-Pr H Br CF₃ CH₃ CF₃ t-Bu H Br CF₃ CH₃ CF₃ Me Me Cl ClCH₃ CF₃ Me H Cl Cl CH₃ CF₃ Et H Cl Cl CH₃ CF₃ i-Pr H Cl Cl CH₃ CF₃ t-BuH Cl Cl CH₃ CF₃ Me Me Br Cl CH₃ CF₃ Me H Br Cl CH₃ CF₃ Et H Br Cl CH₃CF₃ i-Pr H Br Cl CH₃ CF₃ t-Bu H Br Cl CH₃ CF₃ Me Me Cl Br CH₃ CF₃ Me HCl Br CH₃ CF₃ Et H Cl Br CH₃ CF₃ i-Pr H Cl Br CH₃ CF₃ t-Bu H Cl Br CH₃CF₃ Me Me Br Br CH₃ CF₃ Me H Br Br CH₃ CF₃ Et H Br Br CH₃ CF₃ i-Pr H BrBr CH₃ CF₃ t-Bu H Br Br CH₃ CF₃ Me Me Cl OCH₂CF₃ CH₃ CF₃ Me H Cl OCH₂CF₃CH₃ CF₃ Et H Cl OCH₂CF₃ CH₃ CF₃ i-Pr H Cl OCH₂CF₃ CH₃ CF₃ t-Bu H ClOCH₂CF₃ CH₃ CF₃ Me Me Br OCH₂CF₃ CH₃ CF₃ Me H Br OCH₂CF₃ CH₃ CF₃ Et H BrOCH₂CF₃ CH₃ CF₃ i-Pr H Br OCH₂CF₃ CH₃ CF₃ t-Bu H Br OCH₂CF₃ CH₃ CF₃ MeMe Cl Cl CH₃ Cl n-Pr H Cl Cl CH₃ Cl n-Bu H Cl Cl CH₃ Cl s-Bu H Cl Cl CH₃Cl i-Bu H Cl Cl CH₃ Cl Et Me Cl CF₃ F H Me H Cl CF₃ F H Et H Cl CF₃ F Hi-Pr H Cl CF₃ F H t-Bu H Cl CF₃ F H Me Me Br CF₃ F H Me H Br CF₃ F H EtH Br CF₃ F H i-Pr H Br CF₃ F H t-Bu H Br CF₃ F H Me Me Cl Cl F H Me H ClCl F H Et H Cl Cl F H i-Pr H Cl Cl F H t-Bu H Cl Cl F H Me Me Br Cl F HMe H Br Cl F H Et H Br Cl F H i-Pr H Br Cl F H t-Bu H Br Cl F H Me Me ClBr F H Me H Cl Br F H Et H Cl Br F H i-Pr H Cl Br F H t-Bu H Cl Br F HMe Me Br Br F H Me H Br Br F H Et H Br Br F H i-Pr H Br Br F H t-Bu H BrBr F H Me Me Cl OC₂CF₃ F H Me H Cl OCH₂CF₃ F H Et H Cl OCH₂CF₃ F H i-PrH Cl OCH₂CF₃ F H t-Bu H Cl OCH₂CF₃ F H Me Me Br OCH₂CF₃ F H Me H BrOCH₂CF₃ F H Et H Br OCH₂CF₃ F H i-Pr H Br OCH₂CF₃ F H t-Bu H Br OCH₂CF₃F H Me Me Cl CF₃ F F Me H Cl CF₃ F F Et H Cl CF₃ F F i-Pr H Cl CF₃ F Ft-Bu H Cl CF₃ F F Me Me Br CF₃ F F Me H Br CF₃ F F Et H Br CF₃ F F i-PrH Br CF₃ F F t-Bu H Br CF₃ F F Me Me Cl Cl F F Me H Cl Cl F F Et H Cl ClF F i-Pr H Cl Cl F F t-Bu H Cl Cl F F Me Me Br Cl F F Me H Br Cl F F EtH Br Cl F F i-Pr H Br Cl F F t-Bu H Br Cl F F Me Me Cl Br F F Me H Cl BrF F Et H Cl Br F F i-Pr H Cl Br F F t-Bu H Cl Br F F Me Me Br Br F F MeH Br Br F F Et H Br Br F F i-Pr H Br Br F F t-Bu H Br Br F F Me Me ClOCH₂CF₃ F F Me H Cl OCH₂CF₃ F F Et H Cl OCH₂CF₃ F F i-Pr H Cl OCH₂CF₃ FF t-Bu H Cl OCH₂CF₃ F F Me Me Br OCH₂CF₃ F F Me H Br OCH₂CF₃ F F Et H BrOCH₂CF₃ F F i-Pr H Br OCH₂CF₃ F F t-Bu H Br OCH₂CF₃ F F Me Me Cl CF₃ FCl Me H Cl CF₃ F Cl Et H Cl CF₃ F Cl i-Pr H Cl CF₃ F Cl t-Bu H Cl CF₃ FCl Me Me Br CF₃ F Cl Me H Br CF₃ F Cl Et H Br CF₃ F Cl i-Pr H Br CF₃ FCl t-Bu H Br CF₃ F Cl Me Me Cl Cl F Cl Me H Cl Cl F Cl Et H Cl Cl F Cli-Pr H Cl Cl F Cl t-Bu H Cl Cl F Cl Me Me Br Cl F Cl Me H Br Cl F Cl EtH Br Cl F Cl i-Pr H Br Cl F Cl t-Bu H Br Cl F Cl Me Me Cl Br F Cl Me HCl Br F Cl Et H Cl Br F Cl i-Pr H Cl Br F Cl t-Bu H Cl Br F Cl Me Me BrBr F Cl Me H Br Br F Cl Et H Br Br F Cl i-Pr H Br Br F Cl t-Bu H Br Br FCl Me Me Cl OCH₂CF₃ F Cl Me H Cl OCH₂CF₃ F Cl Et H Cl OCH₂CF₃ F Cl i-PrH Cl OCH₂CF₃ F Cl t-Bu H Cl OCH₂CF₃ F Cl Me Me Br OCH₂CF₃ F Cl Me H BrOCH₂CF₃ F Cl Et H Br OCH₂CF₃ F Cl i-Pr H Br OCH₂CF₃ F Cl t-Bu H BrOCH₂CF₃ F Cl Me Me Cl CF₃ F Br Me H Cl CF₃ F Br Et H Cl CF₃ F Br i-Pr HCl CF₃ F Br t-Bu H Cl CF₃ F Br Me Me Br CF₃ F Br Me H Br CF₃ F Br Et HBr CF₃ F Br i-Pr H Br CF₃ F Br t-Bu H Br CF₃ F Br Me Me Cl Cl F Br Me HCl Cl F Br Et H Cl Cl F Br i-Pr H Cl Cl F Br t-Bu H Cl Cl F Br Me Me BrCl F Br Me H Br Cl F Br Et H Br Cl F Br i-Pr H Br Cl F Br t-Bu H Br Cl FBr Me Me Cl Br F Br Me H Cl Br F Br Et H Cl Br F Br i-Pr H Cl Br F Brt-Bu H Cl Br F Br Me Me Br Br F Br Me H Br Br F Br Et H Br Br F Br i-PrH Br Br F Br t-Bu H Br Br F Br Me Me Cl OCH₂CF₃ F Br Me H Cl OCH₂CF₃ FBr Et H Cl OCH₂CF₃ F Br i-Pr H Cl OCH₂CF₃ F Br t-Bu H Cl OCH₂CF₃ F Br MeMe Br OCH₂CF₃ F Br Me H Br OCH₂CF₃ F Br Et H Br OCH₂CF₃ F Br i-Pr H BrOCH₂CF₃ F Br t-Bu H Br OCH₂CF₃ F Br Me Me Cl CF₃ F I Me H Cl CF₃ F I EtH Cl CF₃ F I i-Pr H Cl CF₃ F I t-Bu H Cl CF₃ F I Me Me Br CF₃ F I Me HBr CF₃ F I Et H Br CF₃ F I i-Pr H Br CF₃ F I t-Bu H Br CF₃ F I Me Me ClCl F I Me H Cl Cl F I Et H Cl Cl F I i-Pr H Cl Cl F I t-Bu H Cl Cl F IMe Me Br Cl F I Me H Br Cl F I Et H Br Cl F I i-Pr H Br Cl F I t-Bu H BrCl F I Me Me Cl Br F I Me H Cl Br F I Et H Cl Br F I i-Pr H Cl Br F It-Bu H Cl Br F I Me Me Br Br F I Me H Br Br F I Et H Br Br F I i-Pr H BrBr F I t-Bu H Br Br F I Me Me Cl OCH₂CF₃ F I Me H Cl OCH₂CF₃ F I Et H ClOCH₂CF₃ F I i-Pr H Cl OCH₂CF₃ F I t-Bu H Cl OCH₂CF₃ F I Me Me Br OCH₂CF₃F I Me H Br OCH₂CF₃ F I Et H Br OCH₂CF₃ F I i-Pr H Br OCH₂CF₃ F I t-Bu HBr OCH₂CF₃ F I Me Me Cl CF₃ F CF₃ Me H Cl CF₃ F CF₃ Et H Cl CF₃ F CF₃i-Pr H Cl CF₃ F CF₃ t-Bu H Cl CF₃ F CF₃ Me Me Br CF₃ F CF₃ Me H Br CF₃ FCF₃ Et H Br CF₃ F CF₃ i-Pr H Br CF₃ F CF₃ t-Bu H Br CF₃ F CF₃ Me Me ClCl F CF₃ Me H Cl Cl F CF₃ Et H Cl Cl F CF₃ i-Pr H Cl Cl F CF₃ t-Bu H ClCl F CF₃ Me Me Br Cl F CF₃ Me H Br Cl F CF₃ Et H Br Cl F CF₃ i-Pr H BrCl F CF₃ t-Bu H Br Cl F CF₃ Me Me Cl Br F CF₃ Me H Cl Br F CF₃ Et H ClBr F CF₃ i-Pr H Cl Br F CF₃ t-Bu H Cl Br F CF₃ Me Me Br Br F CF₃ Me H BrBr F CF₃ Et H Br Br F CF₃ i-Pr H Br Br F CF₃ t-Bu H Br Br F CF₃ Me Me ClOCH₂CF₃ F CF₃ Me H Cl OCH₂CF₃ F CF₃ Et H Cl OCH₂CF₃ F CF₃ i-Pr H ClOCH₂CF₃ F CF₃ t-Bu H Cl OCH₂CF₃ F CF₃ Me Me Br OCH₂CF₃ F CF₃ Me H BrOCH₂CF₃ F CF₃ Et H Br OCH₂CF₃ F CF₃ i-Pr H Br OCH₂CF₃ F CF₃ t-Bu H BrOCH₂CF₃ F CF₃ Me Me Cl CF₃ Cl H Me H Cl CF₃ Cl H Et H Cl CF₃ Cl H i-Pr HCl CF₃ Cl H t-Bu H Cl CF₃ Cl H Me Me Br CF₃ Cl H Me H Br CF₃ Cl H Et HBr CF₃ Cl H i-Pr H Br CF₃ Cl H t-Bu H Br CF₃ Cl H Me Me Cl Cl Cl H Me HCl Cl Cl H Et H Cl Cl Cl H i-Pr H Cl Cl Cl H t-Bu H Cl Cl Cl H Me Me BrCl Cl H Me H Br Cl Cl H Et H Br Cl Cl H i-Pr H Br Cl Cl H t-Bu H Br ClCl H Me Me Cl Br Cl H Me H Cl Br Cl H Et H Cl Br Cl H i-Pr H Cl Br Cl Ht-Bu H Cl Br Cl H Me Me Br Br Cl H Me H Br Br Cl H Et H Br Br Cl H i-PrH Br Br Cl H t-Bu H Br Br Cl H Me Me Cl OCH₂CF₃ Cl H Me H Cl OCH₂CF₃ ClH Et H Cl OCH₂CF₃ Cl H i-Pr H Cl OCH₂CF₃ Cl H t-Bu H Cl OCH₂CF₃ Cl H MeMe Br OCH₂CF₃ Cl H Me H Br OCH₂CF₃ Cl H Et H Br OCH₂CF₃ Cl H i-Pr H BrOCH₂CF₃ Cl H t-Bu H Br OCH₂CF₃ Cl H Me Me Cl CF₃ Cl F Me H Cl CF₃ Cl FEt H Cl CF₃ Cl F i-Pr H Cl CF₃ Cl F t-Bu H Cl CF₃ Cl F Me Me Br CF₃ Cl FMe H Br CF₃ Cl F Et H Br CF₃ Cl F i-Pr H Br CF₃ Cl F t-Bu H Br CF₃ Cl FMe Me Cl Cl Cl F Me H Cl Cl Cl F Et H Cl Cl Cl F i-Pr H Cl Cl Cl F t-BuH Cl Cl Cl F Me Me Br Cl Cl F Me H Br Cl Cl F Et H Br Cl Cl F i-Pr H BrCl Cl F t-Bu H Br Cl Cl F Me Me Cl Br Cl F Me H Cl Br Cl F Et H Cl Br ClF i-Pr H Cl Br Cl F t-Bu H Cl Br Cl F Me Me Br Br Cl F Me H Br Br Cl FEt H Br Br Cl F i-Pr H Br Br Cl F t-Bu H Br Br Cl F Me Me Cl OCH₂CF₃ ClF Me H Cl OCH₂CF₃ Cl F Et H Cl OCH₂CF₃ Cl F i-Pr H Cl OCH₂CF₃ Cl F t-BuH Cl OCH₂CF₃ Cl F Me Me Br OCH₂CF₃ Cl F Me H Br OCH₂CF₃ Cl F Et H BrOCH₂CF₃ Cl F i-Pr H Br OCH₂CF₃ Cl F t-Bu H Br OCH₂CF₃ Cl F Me Me Cl CF₃Cl Cl Me H Cl CF₃ Cl Cl Et H Cl CF₃ Cl Cl i-Pr H Cl CF₃ Cl Cl t-Bu H ClCF₃ Cl Cl Me Me Br CF₃ Cl Cl Me H Br CF₃ Cl Cl Et H Br CF₃ Cl Cl i-Pr HBr CF₃ Cl Cl t-Bu H Br CF₃ Cl Cl Me Me Cl Cl Cl Cl Me H Cl Cl Cl Cl Et HCl Cl Cl Cl i-Pr H Cl Cl Cl Cl t-Bu H Cl Cl Cl Cl Me Me Br Cl Cl Cl Me HBr Cl Cl Cl Et H Br Cl Cl Cl i-Pr H Br Cl Cl Cl t-Bu H Br Cl Cl Cl Me MeCl Br Cl Cl Me H Cl Br Cl Cl Et H Cl Br Cl Cl i-Pr H Cl Br Cl Cl t-Bu HCl Br Cl Cl Me Me Br Br Cl Cl Me H Br Br Cl Cl Et H Br Br Cl Cl i-Pr HBr Br Cl Cl t-Bu H Br Br Cl Cl Me Me Cl OCH₂CF₃ Cl Cl Me H Cl OCH₂CF₃ ClCl Et H Cl OCH₂CF₃ Cl Cl i-Pr H Cl OCH₂CF₃ Cl Cl t-Bu H Cl OCH₂CF₃ Cl ClMe Me Br OCH₂CF₃ Cl Cl Me H Br OCH₂CF₃ Cl Cl Et H Br OCH₂CF₃ Cl Cl i-PrH Br OCH₂CF₃ Cl Cl t-Bu H Br OCH₂CF₃ Cl Cl Me Me Cl CF₃ Cl Br Me H ClCF₃ Cl Br Et H Cl CF₃ Cl Br i-Pr H Cl CF₃ Cl Br t-Bu H Cl CF₃ Cl Br MeMe Br CF₃ Cl Br Me H Br CF₃ Cl Br Et H Br CF₃ Cl Br i-Pr H Br CF₃ Cl Brt-Bu H Br CF₃ Cl Br Me Me Cl Cl Cl Br Me H Cl Cl Cl Br Et H Cl Cl Cl Bri-Pr H Cl Cl Cl Br t-Bu H Cl Cl Cl Br Me Me Br Cl Cl Br Me H Br Cl Cl BrEt H Br Cl Cl Br i-Pr H Br Cl Cl Br t-Bu H Br Cl Cl Br Me Me Cl Br Cl BrMe H Cl Br Cl Br Et H Cl Br Cl Br i-Pr H Cl Br Cl Br t-Bu H Cl Br Cl BrMe Me Br Br Cl Br Me H Br Br Cl Br Et H Br Br Cl Br i-Pr H Br Br Cl Brt-Bu H Br Br Cl Br Me Me Cl OCH₂CF₃ Cl Br Me H Cl OCH₂CF₃ Cl Br Et H ClOCH₂CF₃ Cl Br i-Pr H Cl OCH₂CF₃ Cl Br t-Bu H Cl OCH₂CF₃ Cl Br Me Me BrOCH₂CF₃ Cl Br Me H Br OCH₂CF₃ Cl Br Et H Br OCH₂CF₃ Cl Br i-Pr H BrOCH₂CF₃ Cl Br t-Bu H Br OCH₂CF₃ Cl Br Me Me Cl CF₃ Cl I Me H Cl CF₃ Cl IEt H Cl CF₃ Cl I i-Pr H Cl CF₃ Cl I t-Bu H Cl CF₃ Cl I Me Me Br CF₃ Cl IMe H Br CF₃ Cl I Et H Br CF₃ Cl I i-Pr H Br CF₃ Cl I t-Bu H Br CF₃ Cl IMe Me Cl Cl Cl I Me H Cl Cl Cl I Et H Cl Cl Cl I i-Pr H Cl Cl Cl I t-BuH Cl Cl Cl I Me Me Br Cl Cl I Me H Br Cl Cl I Et H Br Cl Cl I i-Pr H BrCl Cl I t-Bu H Br Cl Cl I Me Me Cl Br Cl I Me H Cl Br Cl I Et H Cl Br ClI i-Pr H Cl Br Cl I t-Bu H Cl Br Cl I Me Me Br Br Cl I Me H Br Br Cl IEt H Br Br Cl I i-Pr H Br Br Cl I t-Bu H Br Br Cl I Me Me Cl OCH₂CF₃ ClI Me H Cl OCH₂CF₃ Cl I Et H Cl OCH₂CF₃ Cl I i-Pr H Cl OCH₂CF₃ Cl I t-BuH Cl OCH₂CF₃ Cl I Me Me Br OCH₂CF₃ Cl I Me H Br OCH₂CF₃ Cl I Et H BrOCH₂CF₃ Cl I i-Pr H Br OCH₂CF₃ Cl I t-Bu H Br OCH₂CF₃ Cl I Me Me Cl CF₃Cl CF₃ Me H Cl CF₃ Cl CF₃ Et H Cl CF₃ Cl CF₃ i-Pr H Cl CF₃ Cl CF₃ t-Bu HCl CF₃ Cl CF₃ Me Me Br CF₃ Cl CF₃ Me H Br CF₃ Cl CF₃ Et H Br CF₃ Cl CF₃i-Pr H Br CF₃ Cl CF₃ t-Bu H Br CF₃ Cl CF₃ Me Me Cl Cl Cl CF₃ Me H Cl ClCl CF₃ Et H Cl Cl Cl CF₃ i-Pr H Cl Cl Cl CF₃ t-Bu H Cl Cl Cl CF₃ Me MeBr Cl Cl CF₃ Me H Br Cl Cl CF₃ Et H Br Cl Cl CF₃ i-Pr H Br Cl Cl CF₃t-Bu H Br Cl Cl CF₃ Me Me Cl Br Cl CF₃ Me H Cl Br Cl CF₃ Et H Cl Br ClCF₃ i-Pr H Cl Br Cl CF₃ t-Bu H Cl Br Cl CF₃ Me Me Br Br Cl CF₃ Me H BrBr Cl CF₃ Et H Br Br Cl CF₃ i-Pr H Br Br Cl CF₃ t-Bu H Br Br Cl CF₃ MeMe Cl OCH₂CF₃ Cl CF₃ Me H Cl OCH₂CF₃ Cl CF₃ Et H Cl OCH₂CF₃ Cl CF₃ i-PrH Cl OCH₂CF₃ Cl CF₃ t-Bu H Cl OCH₂CF₃ Cl CF₃ Me Me Br OCH₂CF₃ Cl CF₃ MeH Br OCH₂CF₃ Cl CF₃ Et H Br OCH₂CF₃ Cl CF₃ i-Pr H Br OCH₂CF₃ Cl CF₃ t-BuH Br OCH₂CF₃ Cl CF₃ Me Me Cl Cl Cl Cl n-Pr H Cl Cl Cl Cl n-Bu H Cl Cl ClCl s-Bu H Cl Cl Cl Cl i-Bu H Cl Cl Cl Cl Et Me Cl CF₃ Br H Me H Cl CF₃Br H Et H Cl CF₃ Br H i-Pr H Cl CF₃ Br H t-Bu H Cl CF₃ Br H Me Me Br CF₃Br H Me H Br CF₃ Br H Et H Br CF₃ Br H i-Pr H Br CF₃ Br H t-Bu H Br CF₃Br H Me Me Cl Cl Br H Me H Cl Cl Br H Et H Cl Cl Br H i-Pr H Cl Cl Br Ht-Bu H Cl Cl Br H Me Me Br Cl Br H Me H Br Cl Br H Et H Br Cl Br H i-PrH Br Cl Br H t-Bu H Br Cl Br H Me Me Cl Br Br H Me H Cl Br Br H Et H ClBr Br H i-Pr H Cl Br Br H t-Bu H Cl Br Br H Me Me Br Br Br H Me H Br BrBr H Et H Br Br Br H i-Pr H Br Br Br H t-Bu H Br Br Br H Me Me ClOCH₂CF₃ Br H Me H Cl OCH₂CF₃ Br H Et H Cl OCH₂CF₃ Br H i-Pr H Cl OCH₂CF₃Br H t-Bu H Cl OCH₂CF₃ Br H Me Me Br OCH₂CF₃ Br H Me H Br OCH₂CF₃ Br HEt H Br OCH₂CF₃ Br H i-Pr H Br OCH₂CF₃ Br H t-Bu H Br OCH₂CF₃ Br H Me MeCl CF₃ Br F Me H Cl CF₃ Br F Et H Cl CF₃ Br F i-Pr H Cl CF₃ Br F t-Bu HCl CF₃ Br F Me Me Br CF₃ Br F Me H Br CF₃ Br F Et H Br CF₃ Br F i-Pr HBr CF₃ Br F t-Bu H Br CF₃ Br F Me Me Cl Cl Br F Me H Cl Cl Br F Et H ClCl Br F i-Pr H Cl Cl Br F t-Bu H Cl Cl Br F Me Me Br Cl Br F Me H Br ClBr F Et H Br Cl Br F i-Pr H Br Cl Br F t-Bu H Br Cl Br F Me Me Cl Br BrF Me H Cl Br Br F Et H Cl Br Br F i-Pr H Cl Br Br F t-Bu H Cl Br Br F MeMe Br Br Br F Me H Br Br Br F Et H Br Br Br F i-Pr H Br Br Br F t-Bu HBr Br Br F Me Me Cl OCH₂CF₃ Br F Me H Cl OCH₂CF₃ Br F Et H Cl OCH₂CF₃ BrF i-Pr H Cl OCH₂CF₃ Br F t-Bu H Cl OCH₂CF₃ Br F Me Me Br OCH₂CF₃ Br F MeH Br OCH₂CF₃ Br F Et H Br OCH₂CF₃ Br F i-Pr H Br OCH₂CF₃ Br F t-Bu H BrOCH₂CF₃ Br F Me Me Cl CF₃ Br Cl Me H Cl CF₃ Br Cl Et H Cl CF₃ Br Cl i-PrH Cl CF₃ Br Cl t-Bu H Cl CF₃ Br Cl Me Me Br CF₃ Br Cl Me H Br CF₃ Br ClEt H Br CF₃ Br Cl i-Pr H Br CF₃ Br Cl t-Bu H Br CF₃ Br Cl Me Me Cl Cl BrCl Me H Cl Cl Br Cl Et H Cl Cl Br Cl i-Pr H Cl Cl Br Cl t-Bu H Cl Cl BrCl Me Me Br Cl Br Cl Me H Br Cl Br Cl Et H Br Cl Br Cl i-Pr H Br Cl BrCl t-Bu H Br Cl Br Cl Me Me Cl Br Br Cl Me H Cl Br Br Cl Et H Cl Br BrCl i-Pr H Cl Br Br Cl t-Bu H Cl Br Br Cl Me Me Br Br Br Cl Me H Br Br BrCl Et H Br Br Br Cl i-Pr H Br Br Br Cl t-Bu H Br Br Br Cl Me Me ClOCH₂CF₃ Br Cl Me H Cl OCH₂CF₃ Br Cl Et H Cl OCH₂CF₃ Br Cl i-Pr H ClOCH₂CF₃ Br Cl t-Bu H Cl OCH₂CF₃ Br Cl Me Me Br OCH₂CF₃ Br Cl Me H BrOCH₂CF₃ Br Cl Et H Br OCH₂CF₃ Br Cl i-Pr H Br OCH₂CF₃ Br Cl t-Bu H BrOCH₂CF₃ Br Cl Me Me Cl CF₃ Br Br Me H Cl CF₃ Br Br Et H Cl CF₃ Br Bri-Pr H Cl CF₃ Br Br t-Bu H Cl CF₃ Br Br Me Me Br CF₃ Br Br Me H Br CF₃Br Br Et H Br CF₃ Br Br i-Pr H Br CF₃ Br Br t-Bu H Br CF₃ Br Br Me Me ClCl Br Br Me H Cl Cl Br Br Et H Cl Cl Br Br i-Pr H Cl Cl Br Br t-Bu H ClCl Br Br Me Me Br Cl Br Br Me H Br Cl Br Br Et H Br Cl Br Br i-Pr H BrCl Br Br t-Bu H Br Cl Br Br Me Me Cl Br Br Br Me H Cl Br Br Br Et H ClBr Br Br i-Pr H Cl Br Br Br t-Bu H Cl Br Br Br Me Me Br Br Br Br Me H BrBr Br Br Et H Br Br Br Br i-Pr H Br Br Br Br t-Bu H Br Br Br Br Me Me ClOCH₂CF₃ Br Br Me H Cl OCH₂CF₃ Br Br Et H Cl OCH₂CF₃ Br Br i-Pr H ClOCH₂CF₃ Br Br t-Bu H Cl OCH₂CF₃ Br Br Me Me Br OCH₂CF₃ Br Br Me H BrOCH₂CF₃ Br Br Et H Br OCH₂CF₃ Br Br i-Pr H Br OCH₂CF₃ Br Br t-Bu H BrOCH₂CF₃ Br Br Me Me Cl CF₃ Br I Me H Cl CF₃ Br I Et H Cl CF₃ Br I i-Pr HCl CF₃ Br I t-Bu H Cl CF₃ Br I Me Me Br CF₃ Br I Me H Br CF₃ Br I Et HBr CF₃ Br I i-Pr H Br CF₃ Br I t-Bu H Br CF₃ Br I Me Me Cl Cl Br I Me HCl Cl Br I Et H Cl Cl Br I i-Pr H Cl Cl Br I t-Bu H Cl Cl Br I Me Me BrCl Br I Me H Br Cl Br I Et H Br Cl Br I i-Pr H Br Cl Br I t-Bu H Br ClBr I Me Me Cl Br Br I Me H Cl Br Br I Et H Cl Br Br I i-Pr H Cl Br Br It-Bu H Cl Br Br I Me Me Br Br Br I Me H Br Br Br I Et H Br Br Br I i-PrH Br Br Br I t-Bu H Br Br Br I Me Me Cl OCH₂CF₃ Br I Me H Cl OCH₂CF₃ BrI Et H Cl OCH₂CF₃ Br I i-Pr H Cl OCH₂CF₃ Br I t-Bu H Cl OCH₂CF₃ Br I MeMe Br OCH₂CF₃ Br I Me H Br OCH₂CF₃ Br I Et H Br OCH₂CF₃ Br I i-Pr H BrOCH₂CF₃ Br I t-Bu H Br OCH₂CF₃ Br I Me Me Cl CF₃ Br CF₃ Me H Cl CF₃ BrCF₃ Et H Cl CF₃ Br CF₃ i-Pr H Cl CF₃ Br CF₃ t-Bu H Cl CF₃ Br CF₃ Me MeBr CF₃ Br CF₃ Me H Br CF₃ Br CF₃ Et H Br CF₃ Br CF₃ i-Pr H Br CF₃ Br CF₃t-Bu H Br CF₃ Br CF₃ Me Me Cl Cl Br CF₃ Me H Cl Cl Br CF₃ Et H Cl Cl BrCF₃ i-Pr H Cl Cl Br CF₃ t-Bu H Cl Cl Br CF₃ Me Me Br Cl Br CF₃ Me H BrCl Br CF₃ Et H Br Cl Br CF₃ i-Pr H Br Cl Br CF₃ t-Bu H Br Cl Br CF₃ MeMe Cl Br Br CF₃ Me H Cl Br Br CF₃ Et H Cl Br Br CF₃ i-Pr H Cl Br Br CF₃t-Bu H Cl Br Br CF₃ Me Me Br Br Br CF₃ Me H Br Br Br CF₃ Et H Br Br BrCF₃ i-Pr H Br Br Br CF₃ t-Bu H Br Br Br CF₃ Me Me Cl OCH₂CF₃ Br CF₃ Me HCl OCH₂CF₃ Br CF₃ Et H Cl OCH₂CF₃ Br CF₃ i-Pr H Cl OCH₂CF₃ Br CF₃ t-Bu HCl OCH₂CF₃ Br CF₃ Me Me Br OCH₂CF₃ Br CF₃ Me H Br OCH₂CF₃ Br CF₃ Et H BrOCH₂CF₃ Br CF₃ i-Pr H Br OCH₂CF₃ Br CF₃ t-Bu H Br OCH₂CF₃ Br CF₃ Me Me

[0257] TABLE 5

R⁶(a) R⁵(a) R⁴(a) R⁴(b) R³ R² Cl CF₃ CH₃ H Me H Cl CF₃ CH₃ H Et H Cl CF₃CH₃ H i-Pr H Cl CF₃ CH₃ H t-Bu H Cl CF₃ CH₃ H Me Me Br CF₃ CH₃ H Me H BrCF₃ CH₃ H Et H Br CF₃ CH₃ H i-Pr H Br CF₃ CH₃ H t-Bu H Br CF₃ CH₃ H MeMe Cl Cl CH₃ H Me H Cl Cl CH₃ H Et H Cl Cl CH₃ H i-Pr H Cl Cl CH₃ H t-BuH Cl Cl CH₃ H Me Me Br Cl CH₃ H Me H Br Cl CH₃ H Et H Br Cl CH₃ H i-Pr HBr Cl CH₃ H t-Bu H Br Cl CH₃ H Me Me Cl Br CH₃ H Me H Cl Br CH₃ H Et HCl Br CH₃ H i-Pr H Cl Br CH₃ H t-Bu H Cl Br CH₃ H Me Me Br Br CH₃ H Me HBr Br CH₃ H Et H Br Br CH₃ H i-Pr H Br Br CH₃ H t-Bu H Br Br CH₃ H Me MeCl OCH₂CF₃ CH₃ H Me H Cl OCH₂CF₃ CH₃ H Et H Cl OCH₂CF₃ CH₃ H i-Pr H ClOCH₂CF₃ CH₃ H t-Bu H Cl OCH₂CF₃ CH₃ H Me Me Br OCH₂CF₃ CH₃ H Me H BrOCH₂CF₃ CH₃ H Et H Br OCH₂CF₃ CH₃ H i-Pr H Br OCH₂CF₃ CH₃ H t-Bu H BrOCH₂CF₃ CH₃ H Me Me Cl CF₃ CH₃ F Me H Cl CF₃ CH₃ F Et H Cl CF₃ CH₃ Fi-Pr H Cl CF₃ CH₃ F t-Bu H Cl CF₃ CH₃ F Me Me Br CF₃ CH₃ F Me H Br CF₃CH₃ F Et H Br CF₃ CH₃ F i-Pr H Br CF₃ CH₃ F t-Bu H Br CF₃ CH₃ F Me Me ClCl CH₃ F Me H Cl Cl CH₃ F Et H Cl Cl CH₃ F i-Pr H Cl Cl CH₃ F t-Bu H ClCl CH₃ F Me Me Br Cl CH₃ F Me H Br Cl CH₃ F Et H Br Cl CH₃ F i-Pr H BrCl CH₃ F t-Bu H Br Cl CH₃ F Me Me Cl Br CH₃ F Me H Cl Br CH₃ F Et H ClBr CH₃ F i-Pr H Cl Br CH₃ F t-Bu H Cl Br CH₃ F Me Me Br Br CH₃ F Me H BrBr CH₃ F Et H Br Br CH₃ F i-Pr H Br Br CH₃ F t-Bu H Br Br CH₃ F Me Me ClOCH₂CF₃ CH₃ F Me H Cl OCH₂CF₃ CH₃ F Et H Cl OCH₂CF₃ CH₃ F i-Pr H ClOCH₂CF₃ CH₃ F t-Bu H Cl OCH₂CF₃ CH₃ F Me Me Br OCH₂CF₃ CH₃ F Me H BrOCH₂CF₃ CH₃ F Et H Br OCH₂CF₃ CH₃ F i-Pr H Br OCH₂CF₃ CH₃ F t-Bu H BrOCH₂CF₃ CH₃ F Me Me Cl CF₃ CH₃ Cl Me H Cl CF₃ CH₃ Cl Et H Cl CF₃ CH₃ Cli-Pr H Cl CF₃ CH₃ Cl t-Bu H Cl CF₃ CH₃ Cl Me Me Br CF₃ CH₃ Cl Me H BrCF₃ CH₃ Cl Et H Br CF₃ CH₃ Cl i-Pr H Br CF₃ CH₃ Cl t-Bu H Br CF₃ CH₃ ClMe Me Cl Cl CH₃ Cl Me H Cl Cl CH₃ Cl Et H Cl Cl CH₃ Cl i-Pr H Cl Cl CH₃Cl t-Bu H Cl Cl CH₃ Cl Me Me Br Cl CH₃ Cl Me H Br Cl CH₃ Cl Et H Br ClCH₃ Cl i-Pr H Br Cl CH₃ Cl t-Bu H Br Cl CH₃ Cl Me Me Cl Br CH₃ Cl Me HCl Br CH₃ Cl Et H Cl Br CH₃ Cl i-Pr H Cl Br CH₃ Cl t-Bu H Cl Br CH₃ ClMe Me Br Br CH₃ Cl Me H Br Br CH₃ Cl Et H Br Br CH₃ Cl i-Pr H Br Br CH₃Cl t-Bu H Br Br CH₃ Cl Me Me Cl OCH₂CF₃ CH₃ Cl Me H Cl OCH₂CF₃ CH₃ Cl EtH Cl OCH₂CF₃ CH₃ Cl i-Pr H Cl OCH₂CF₃ CH₃ Cl t-Bu H Cl OCH₂CF₃ CH₃ Cl MeMe Br OCH₂CF₃ CH₃ Cl Me H Br OCH₂CF₃ CH₃ Cl Et H Br OCH₂CF₃ CH₃ Cl i-PrH Br OCH₂CF₃ CH₃ Cl t-Bu H Br OCH₂CF₃ CH₃ Cl Me Me Cl CF₃ CH₃ Br Me H ClCF₃ CH₃ Br Et H Cl CF₃ CH₃ Br i-Pr H Cl CF₃ CH₃ Br t-Bu H Cl CF₃ CH₃ BrMe Me Br CF₃ CH₃ Br Me H Br CF₃ CH₃ Br Et H Br CF₃ CH₃ Br i-Pr H Br CF₃CH₃ Br t-Bu H Br CF₃ CH₃ Br Me Me Cl Cl CH₃ Br Me H Cl Cl CH₃ Br Et H ClCl CH₃ Br i-Pr H Cl Cl CH₃ Br t-Bu H Cl Cl CH₃ Br Me Me Br Cl CH₃ Br MeH Br Cl CH₃ Br Et H Br Cl CH₃ Br i-Pr H Br Cl CH₃ Br t-Bu H Br Cl CH₃ BrMe Me Cl Br CH₃ Br Me H Cl Br CH₃ Br Et H Cl Br CH₃ Br i-Pr H Cl Br CH₃Br t-Bu H Cl Br CH₃ Br Me Me Br Br CH₃ Br Me H Br Br CH₃ Br Et H Br BrCH₃ Br i-Pr H Br Br CH₃ Br t-Bu H Br Br CH₃ Br Me Me Cl OCH₂CF₃ CH₃ BrMe H Cl OCH₂CF₃ CH₃ Br Et H Cl OCH₂CF₃ CH₃ Br i-Pr H Cl OCH₂CF₃ CH₃ Brt-Bu H Cl OCH₂CF₃ CH₃ Br Me Me Br OCH₂CF₃ CH₃ Br Me H Br OCH₂CF₃ CH₃ BrEt H Br OCH₂CF₃ CH₃ Br i-Pr H Br OCH₂CF₃ CH₃ Br t-Bu H Br OCH₂CF₃ CH₃ BrMe Me Cl CF₃ CH₃ I Me H Cl CF₃ CH₃ I Et H Cl CF₃ CH₃ I i-Pr H Cl CF₃ CH₃I t-Bu H Cl CF₃ CH₃ I Me Me Br CF₃ CH₃ I Me H Br CF₃ CH₃ I Et H Br CF₃CH₃ I i-Pr H Br CF₃ CH₃ I t-Bu H Br CF₃ CH₃ I Me Me Cl Cl CH₃ I Me H ClCl CH₃ I Et H Cl Cl CH₃ I i-Pr H Cl Cl CH₃ I t-Bu H Cl Cl CH₃ I Me Me BrCl CH₃ I Me H Br Cl CH₃ I Et H Br Cl CH₃ I i-Pr H Br Cl CH₃ I t-Bu H BrCl CH₃ I Me Me Cl Br CH₃ I Me H Cl Br CH₃ I Et H Cl Br CH₃ I i-Pr H ClBr CH₃ I t-Bu H Cl Br CH₃ I Me Me Br Br CH₃ I Me H Br Br CH₃ I Et H BrBr CH₃ I i-Pr H Br Br CH₃ I t-Bu H Br Br CH₃ I Me Me Cl OCH₂CF₃ CH₃ I MeH Cl OCH₂CF₃ CH₃ I Et H Cl OCH₂CF₃ CH₃ I i-Pr H Cl OCH₂CF₃ CH₃ I t-Bu HCl OCH₂CF₃ CH₃ I Me Me Br OCH₂CF₃ CH₃ I Me H Br OCH₂CF₃ CH₃ I Et H BrOCH₂CF₃ CH₃ I i-Pr H Br OCH₂CF₃ CH₃ I t-Bu H Br OCH₂CF₃ CH₃ I Me Me ClCF₃ CH₃ CH₃ Me H Cl CF₃ CH₃ CH₃ Et H Cl CF₃ CH₃ CH₃ i-Pr H Cl CF₃ CH₃CH₃ t-Bu H Cl CF₃ CH₃ CH₃ Me Me Br CF₃ CH₃ CH₃ Me H Br CF₃ CH₃ CH₃ Et HBr CF₃ CH₃ CH₃ i-Pr H Br CF₃ CH₃ CH₃ t-Bu H Br CF₃ CH₃ CH₃ Me Me Cl ClCH₃ CH₃ Me H Cl Cl CH₃ CH₃ Et H Cl Cl CH₃ CH₃ i-Pr H Cl Cl CH₃ CF₃ t-BuH Cl Cl CH₃ CF₃ Me Me Br Cl CH₃ CF₃ Me H Br Cl CH₃ CF₃ Et H Br Cl CH₃CF₃ i-Pr H Br Cl CH₃ CF₃ t-Bu H Br Cl CH₃ CF₃ Me Me Cl Br CH₃ CF₃ Me HCl Br CH₃ CF₃ Et H Cl Br CH₃ CF₃ i-Pr H Cl Br CH₃ CF₃ t-Bu H Cl Br CH₃CF₃ Me Me Br Br CH₃ CF₃ Me H Br Br CH₃ CF₃ Et H Br Br CH₃ CF₃ i-Pr H BrBr CH₃ CF₃ t-Bu H Br Br CH₃ CF₃ Me Me Cl OCH₂CF₃ CH₃ CF₃ Me H Cl OCH₂CF₃CH₃ CF₃ Et H Cl OCH₂CF₃ CH₃ CF₃ i-Pr H Cl OCH₂CF₃ CH₃ CF₃ t-Bu H ClOCH₂CF₃ CH₃ CF₃ Me Me Br OCH₂CF₃ CH₃ CF₃ Me H Br OCH₂CF₃ CH₃ CF₃ Et H BrOCH₂CF₃ CH₃ CF₃ i-Pr H Br OCH₂CF₃ CH₃ CF₃ t-Bu H Br OCH₂CF₃ CH₃ CF₃ MeMe Cl Cl CH₃ Cl n-Pr H Cl Cl CH₃ Cl n-Bu H Cl Cl CH₃ Cl s-Bu H Cl Cl CH₃Cl i-Bu H Cl Cl CH₃ Cl Et Me Cl CF₃ F H Me H Cl CF₃ F H Et H Cl CF₃ F Hi-Pr H Cl CF₃ F H t-Bu H Cl CF₃ F H Me Me Br CF₃ F H Me H Br CF₃ F H EtH Br CF₃ F H i-Pr H Br CF₃ F H t-Bu H Br CF₃ F H Me Me Cl Cl F H Me H ClCl F H Et H Cl Cl F H i-Pr H Cl Cl F H t-Bu H Cl Cl F H Me Me Br Cl F HMe H Br Cl F H Et H Br Cl F H i-Pr H Br Cl F H t-Bu H Br Cl F H Me Me ClBr F H Me H Cl Br F H Et H Cl Br F H i-Pr H Cl Br F H t-Bu H Cl Br F HMe Me Br Br F H Me H Br Br F H Et H Br Br F H i-Pr H Br Br F H t-Bu H BrBr F H Me Me Cl OCH₂CF₃ F H Me H Cl OCH₂CF₃ F H Et H Cl OCH₂CF₃ F H i-PrH Cl OCH₂CF₃ F H t-Bu H Cl OCH₂CF₃ F H Me Me Br OCH₂CF₃ F H Me H BrOCH₂CF₃ F H Et H Br OCH₂CF₃ F H i-Pr H Br OCH₂CF₃ F H t-Bu H Br OCH₂CF₃F H Me Me Cl CF₃ F F Me H Cl CF₃ F F Et H Cl CF₃ F F i-Pr H Cl CF₃ F Ft-Bu H Cl CF₃ F F Me Me Br CF₃ F F Me H Br CF₃ F F Et H Br CF₃ F F i-PrH Br CF₃ F F t-Bu H Br CF₃ F F Me Me Cl Cl F F Me H Cl Cl F F Et H Cl ClF F i-Pr H Cl Cl F F t-Bu H Cl Cl F F Me Me Br Cl F F Me H Br Cl F F EtH Br Cl F F i-Pr H Br Cl F F t-Bu H Br Cl F F Me Me Cl Br F F Me H Cl BrF F Et H Cl Br F F i-Pr H Cl Br F F t-Bu H Cl Br F F Me Me Br Br F F MeH Br Br F F Et H Br Br F F i-Pr H Br Br F F t-Bu H Br Br F F Me Me ClOCH₂CF₃ F F Me H Cl OCH₂CF₃ F F Et H Cl OCH₂CF₃ F F i-Pr H Cl OCH₂CF₃ FF t-Bu H Cl OCH₂CF₃ F F Me Me Br OCH₂CF₃ F F Me H Br OCH₂CF₃ F F Et H BrOCH₂CF₃ F F i-Pr H Br OCH₂CF₃ F F t-Bu H Br OCH₂CF₃ F Cl Me Me Cl CF₃ FCl Me H Cl CF₃ F Cl Et H Cl CF₃ F Cl i-Pr H Cl CF₃ F Cl t-Bu H Cl CF₃ FCl Me Me Br CF₃ F Cl Me H Br CF₃ F Cl Et H Br CF₃ F Cl i-Pr H Br CF₃ FCl t-Bu H Br CF₃ F Cl Me Me Cl Cl F Cl Me H Cl Cl F Cl Et H Cl Cl F Cli-Pr H Cl Cl F Cl t-Bu H Cl Cl F Cl Me Me Br Cl F Cl Me H Br Cl F Cl EtH Br Cl F Cl i-Pr H Br Cl F Cl t-Bu H Br Cl F Cl Me Me Cl Br F Cl Me HCl Br F Cl Et H Cl Br F Cl i-Pr H Cl Br F Cl t-Bu H Cl Br F Cl Me Me BrBr F Cl Me H Br Br F Cl Et H Br Br F Cl i-Pr H Br Br F Cl t-Bu H Br Br FCl Me Me Cl OCH₂CF₃ F Cl Me H Cl OCH₂CF₃ F Cl Et H Cl OCH₂CF₃ F Cl i-PrH Cl OCH₂CF₃ F Cl t-Bu H Cl OCH₂CF₃ F Cl Me Me Br OCH₂CF₃ F Cl Me H BrOCH₂CF₃ F Cl Et H Br OCH₂CF₃ F Cl i-Pr H Br OCH₂CF₃ F Cl t-Bu H BrOCH₂CF₃ F Cl Me Me Cl CF₃ F Br Me H Cl CF₃ F Br Et H Cl CF₃ F Br i-Pr HCl CF₃ F Br t-Bu H Cl CF₃ F Br Me Me Br CF₃ F Br Me H Br CF₃ F Br Et HBr CF₃ F Br i-Pr H Br CF₃ F Br t-Bu H Br CF₃ F Br Me Me Cl Cl F Br Me HCl Cl F Br Et H Cl Cl F Br i-Pr H Cl Cl F Br t-Bu H Cl Cl F Br Me Me BrCl F Br Me H Br Cl F Br Et H Br Cl F Br i-Pr H Br Cl F Br t-Bu H Br Cl FBr Me Me Cl Br F Br Me H Cl Br F Br Et H Cl Br F Br i-Pr H Cl Br F Brt-Bu H Cl Br F Br Me Me Br Br F Br Me H Br Br F Br Et H Br Br F Br i-PrH Br Br F Br t-Bu H Br Br F Br Me Me Cl OCH₂CF₃ F Br Me H Cl OCH₂CF₃ FBr Et H Cl OCH₂CF₃ F Br i-Pr H Cl OCH₂CF₃ F Br t-Bu H Cl OCH₂CF₃ F Br MeMe Br OCH₂CF₃ F Br Me H Br OCH₂CF₃ F Br Et H Br OCH₂CF₃ F Br i-Pr H BrOCH₂CF₃ F Br t-Bu H Br OCH₂CF₃ F Br Me Me Cl CF₃ F I Me H Cl CF₃ F I EtH Cl CF₃ F I i-Pr H Cl CF₃ F I t-Bu H Cl CF₃ F I Me Me Br CF₃ F I Me HBr CF₃ F I Et H Br CF₃ F I i-Pr H Br CF₃ F I t-Bu H Br CF₃ F I Me Me ClCl F I Me H Cl Cl F I Et H Cl Cl F I i-Pr H Cl Cl F I t-Bu H Cl Cl F IMe Me Br Cl F I Me H Br Cl F I Et H Br Cl F I i-Pr H Br Cl F I t-Bu H BrCl F I Me Me Cl Br F I Me H Cl Br F I Et H Cl Br F I i-Pr H Cl Br F It-Bu H Cl Br F I Me Me Br Br F I Me H Br Br F I Et H Br Br F I i-Pr H BrBr F I t-Bu H Br Br F I Me Me Cl OCH₂CF₃ F I Me H Cl OCH₂CF₃ F I Et H ClOCH₂CF₃ F I i-Pr H Cl OCH₂CF₃ F I t-Bu H Cl OCH₂CF₃ F I Me Me Br OCH₂CF₃F I Me H Br OCH₂CF₃ F I Et H Br OCH₂CF₃ F I i-Pr H Br OCH₂CF₃ F I t-Bu HBr OCH₂CF₃ F I Me Me Cl CF₃ F CF₃ Me H Cl CF₃ F CF₃ Et H Cl CF₃ F CF₃i-Pr H Cl CF₃ F CF₃ t-Bu H Cl CF₃ F CF₃ Me Me Br CF₃ F CF₃ Me H Br CF₃ FCF₃ Et H Br CF₃ F CF₃ i-Pr H Br CF₃ F CF₃ t-Bu H Br CF₃ F CF₃ Me Me ClCl F CF₃ Me H Cl Cl F CF₃ Et H Cl Cl F CF₃ i-Pr H Cl Cl F CF₃ t-Bu H ClCl F CF₃ Me Me Br Cl F CF₃ Me H Br Cl F CF₃ Et H Br Cl F CF₃ i-Pr H BrCl F CF₃ t-Bu H Br Cl F CF₃ Me Me Cl Br F CF₃ Me H Cl Br F CF₃ Et H ClBr F CF₃ i-Pr H Cl Br F CF₃ t-Bu H Cl Br F CF₃ Me Me Br Br F CF₃ Me H BrBr F CF₃ Et H Br Br F CF₃ i-Pr H Br Br F CF₃ t-Bu H Br Br F CF₃ Me Me ClOCH₂CF₃ F CF₃ Me H Cl OCH₂CF₃ F CF₃ Et H Cl OCH₂CF₃ F CF₃ i-Pr H ClOCH₂CF₃ F CF₃ t-Bu H Cl OCH₂CF₃ F CF₃ Me Me Br OCH₂CF₃ F CF₃ Me H BrOCH₂CF₃ F CF₃ Et H Br OCH₂CF₃ F CF₃ i-Pr H Br OCH₂CF₃ F CF₃ t-Bu H BrOCH₂CF₃ F CF₃ Me Me Cl CF₃ Cl H Me H Cl CF₃ Cl H Et H Cl CF₃ Cl H i-Pr HCl CF₃ Cl H t-Bu H Cl CF₃ Cl H Me Me Br CF₃ Cl H Me H Br CF₃ Cl H Et HBr CF₃ Cl H i-Pr H Br CF₃ Cl H t-Bu H Br CF₃ Cl H Me Me Cl Cl Cl H Me HCl Cl Cl H Et H Cl Cl Cl H i-Pr H Cl Cl Cl H t-Bu H Cl Cl Cl H Me Me BrCl Cl H Me H Br Cl Cl H Et H Br Cl Cl H i-Pr H Br Cl Cl H t-Bu H Br ClCl H Me Me Cl Br Cl H Me H Cl Br Cl H Et H Cl Br Cl H i-Pr H Cl Br Cl Ht-Bu H Cl Br Cl H Me Me Br Br Cl H Me H Br Br Cl H Et H Br Br Cl H i-PrH Br Br Cl H t-Bu H Br Br Cl H Me Me Cl OCH₂CF₃ Cl H Me H Cl OCH₂CF₃ ClH Et H Cl OCH₂CF₃ Cl H i-Pr H Cl OCH₂CF₃ Cl H t-Bu H Cl OCH₂CF₃ Cl H MeMe Br OCH₂CF₃ Cl H Me H Br OCH₂CF₃ Cl H Et H Br OCH₂CF₃ Cl H i-Pr H BrOCH₂CF₃ Cl H t-Bu H Br OCH₂CF₃ Cl H Me Me Cl CF₃ Cl F Me H Cl CF₃ Cl FEt H Cl CF₃ Cl F i-Pr H Cl CF₃ Cl F t-Bu H Cl CF₃ Cl F Me Me Br CF₃ Cl FMe H Br CF₃ Cl F Et H Br CF₃ Cl F i-Pr H Br CF₃ Cl F t-Bu H Br CF₃ Cl FMe Me Cl Cl Cl F Me H Cl Cl Cl F Et H Cl Cl Cl F i-Pr H Cl Cl Cl F t-BuH Cl Cl Cl F Me Me Br Cl Cl F Me H Br Cl Cl F Et H Br Cl Cl F i-Pr H BrCl Cl F t-Bu H Br Cl Cl F Me Me Cl Br Cl F Me H Cl Br Cl F Et H Cl Br ClF i-Pr H Cl Br Cl F t-Bu H Cl Br Cl F Me Me Br Br Cl F Me H Br Br Cl FEt H Br Br Cl F i-Pr H Br Br Cl F t-Bu H Br Br Cl F Me Me Cl OCH₂CF₃ ClF Me H Cl OCH₂CF₃ Cl F Et H Cl OCH₂CF₃ Cl F i-Pr H Cl OCH₂CF₃ Cl F t-BuH Cl OCH₂CF₃ Cl F Me Me Br OCH₂CF₃ Cl F Me H Br OCH₂CF₃ Cl F Et H BrOCH₂CF₃ Cl F i-Pr H Br OCH₂CF₃ Cl F t-Bu H Br OCH₂CF₃ Cl F Me Me Cl CF₃Cl Cl Me H Cl CF₃ Cl Cl Et H Cl CF₃ Cl Cl i-Pr H Cl CF₃ Cl Cl t-Bu H ClCF₃ Cl Cl Me Me Br CF₃ Cl Cl Me H Br CF₃ Cl Cl Et H Br CF₃ Cl Cl i-Pr HBr CF₃ Cl Cl t-Bu H Br CF₃ Cl Cl Me Me Cl Cl Cl Cl Me H Cl Cl Cl Cl Et HCl Cl Cl Cl i-Pr H Cl Cl Cl Cl t-Bu H Cl Cl Cl Cl Me Me Br Cl Cl Cl Me HBr Cl Cl Cl Et H Br Cl Cl Cl i-Pr H Br Cl Cl Cl t-Bu H Br Cl Cl Cl Me MeCl Br Cl Cl Me H Cl Br Cl Cl Et H Cl Br Cl Cl i-Pr H Cl Br Cl Cl t-Bu HCl Br Cl Cl Me Me Br Br Cl Cl Me H Br Br Cl Cl Et H Br Br Cl Cl i-Pr HBr Br Cl Cl t-Bu H Br Br Cl Cl Me Me Cl OCH₂CF₃ Cl Cl Me H Cl OCH₂CF₃ ClCl Et H Cl OCH₂CF₃ Cl Cl i-Pr H Cl OCH₂CF₃ Cl Cl t-Bu H Cl OCH₂CF₃ Cl ClMe Me Br OCH₂CF₃ Cl Cl Me H Br OCH₂CF₃ Cl Cl Et H Br OCH₂CF₃ Cl Cl i-PrH Br OCH₂CF₃ Cl Cl t-Bu H Br OCH₂CF₃ Cl Cl Me Me Cl CF₃ Cl Br Me H ClCF₃ Cl Br Et H Cl CF₃ Cl Br i-Pr H Cl CF₃ Cl Br t-Bu H Cl CF₃ Cl Br MeMe Br CF₃ Cl Br Me H Br CF₃ Cl Br Et H Br CF₃ Cl Br i-Pr H Br CF₃ Cl Brt-Bu H Br CF₃ Cl Br Me Me Cl Cl Cl Br Me H Cl Cl Cl Br Et H Cl Cl Cl Bri-Pr H Cl Cl Cl Br t-Bu H Cl Cl Cl Br Me Me Br Cl Cl Br Me H Br Cl Cl BrEt H Br Cl Cl Br i-Pr H Br Cl Cl Br t-Bu H Br Cl Cl Br Me Me Cl Br Cl BrMe H Cl Br Cl Br Et H Cl Br Cl Br i-Pr H Cl Br Cl Br t-Bu H Cl Br Cl BrMe Me Br Br Cl Br Me H Br Br Cl Br Et H Br Br Cl Br i-Pr H Br Br Cl Brt-Bu H Br Br Cl Br Me Me Cl OCH₂CF₃ Cl Br Me H Cl OCH₂CF₃ Cl Br Et H ClOCH₂CF₃ Cl Br i-Pr H Cl OCH₂CF₃ Cl Br t-Bu H Cl OCH₂CF₃ Cl Br Me Me BrOCH₂CF₃ Cl Br Me H Br OCH₂CF₃ Cl Br Et H Br OCH₂CF₃ Cl Br i-Pr H BrOCH₂CF₃ Cl Br t-Bu H Br OCH₂CF₃ Cl Br Me Me Cl CF₃ Cl I Me H Cl CF₃ Cl IEt H Cl CF₃ Cl I i-Pr H Cl CF₃ Cl I t-Bu H Cl CF₃ Cl I Me Me Br CF₃ Cl IMe H Br CF₃ Cl I Et H Br CF₃ Cl I i-Pr H Br CF₃ Cl I t-Bu H Br CF₃ Cl IMe Me Cl Cl Cl I Me H Cl Cl Cl I Et H Cl Cl Cl I i-Pr H Cl Cl Cl I t-BuH Cl Cl Cl I Me Me Br Cl Cl I Me H Br Cl Cl I Et H Br Cl Cl I i-Pr H BrCl Cl I t-Bu H Br Cl Cl I Me Me Cl Br Cl I Me H Cl Br Cl I Et H Cl Br ClI i-Pr H Cl Br Cl I t-Bu H Cl Br Cl I Me Me Br Br Cl I Me H Br Br Cl IEt H Br Br Cl I i-Pr H Br Br Cl I t-Bu H Br Br Cl I Me Me Cl OCH₂CF₃ ClI Me H Cl OCH₂CF₃ Cl I Et H Cl OCH₂CF₃ Cl I i-Pr H Cl OCH₂CF₃ Cl I t-BuH Cl OCH₂CF₃ Cl I Me Me Br OCH₂CF₃ Cl I Me H Br OCH₂CF₃ Cl I Et H BrOCH₂CF₃ Cl I i-Pr H Br OCH₂CF₃ Cl I t-Bu H Br OCH₂CF₃ Cl I Me Me Cl CF₃Cl CF₃ Me H Cl CF₃ Cl CF₃ Et H Cl CF₃ Cl CF₃ i-Pr H Cl CF₃ Cl CF₃ t-Bu HCl CF₃ Cl CF₃ Me Me Br CF₃ Cl CF₃ Me H Br CF₃ Cl CF₃ Et H Br CF₃ Cl CF₃i-Pr H Br CF₃ Cl CF₃ t-Bu H Br CF₃ Cl CF₃ Me Me Cl Cl Cl CF₃ Me H Cl ClCl CF₃ Et H Cl Cl Cl CF₃ i-Pr H Cl Cl Cl CF₃ t-Bu H Cl Cl Cl CF₃ Me MeBr Cl Cl CF₃ Me H Br Cl Cl CF₃ Et H Br Cl Cl CF₃ i-Pr H Br Cl Cl CF₃t-Bu H Br Cl Cl CF₃ Me Me Cl Br Cl CF₃ Me H Cl Br Cl CF₃ Et H Cl Br ClCF₃ i-Pr H Cl Br Cl CF₃ t-Bu H Cl Br Cl CF₃ Me Me Br Br Cl CF₃ Me H BrBr Cl CF₃ Et H Br Br Cl CF₃ i-Pr H Br Br Cl CF₃ t-Bu H Br Br Cl CF₃ MeMe Cl OCH₂CF₃ Cl CF₃ Me H Cl OCH₂CF₃ Cl CF₃ Et H Cl OCH₂CF₃ Cl CF₃ i-PrH Cl OCH₂CF₃ Cl CF₃ t-Bu H Cl OCH₂CF₃ Cl CF₃ Me Me Br OCH₂CF₃ Cl CF₃ MeH Br OCH₂CF₃ Cl CF₃ Et H Br OCH₂CF₃ Cl CF₃ i-Pr H Br OCH₂CF₃ Cl CF₃ t-BuH Br OCH₂CF₃ Cl CF₃ Me Me Cl Cl Cl Cl n-Pr H Cl Cl Cl Cl n-Bu H Cl Cl ClCl s-Bu H Cl Cl Cl Cl i-Bu H Cl Cl Cl Cl Et Me Cl CF₃ Br H Me H Cl CF₃Br H Et H Cl CF₃ Br H i-Pr H Cl CF₃ Br H t-Bu H Cl CF₃ Br H Me Me Br CF₃Br H Me H Br CF₃ Br H Et H Br CF₃ Br H i-Pr H Br CF₃ Br H t-Bu H Br CF₃Br H Me Me Cl Cl Br H Me H Cl Cl Br H Et H Cl Cl Br H i-Pr H Cl Cl Br Ht-Bu H Cl Cl Br H Me Me Br Cl Br H Me H Br Cl Br H Et H Br Cl Br H i-PrH Br Cl Br H t-Bu H Br Cl Br H Me Me Cl Br Br H Me H Cl Br Br H Et H ClBr Br H i-Pr H Cl Br Br H t-Bu H Cl Br Br H Me Me Br Br Br H Me H Br BrBr H Et H Br Br Br H i-Pr H Br Br Br H t-Bu H Br Br Br H Me Me ClOCH₂CF₃ Br H Me H Cl OCH₂CF₃ Br H Et H Cl OCH₂CF₃ Br H i-Pr H Cl OCH₂CF₃Br H t-Bu H Cl OCH₂CF₃ Br H Me Me Br OCH₂CF₃ Br H Me H Br OCH₂CF₃ Br HEt H Br OCH₂CF₃ Br H i-Pr H Br OCH₂CF₃ Br H t-Bu H Br OCH₂CF₃ Br H Me MeCl CF₃ Br F Me H Cl CF₃ Br F Et H Cl CF₃ Br F i-Pr H Cl CF₃ Br F t-Bu HCl CF₃ Br F Me Me Br CF₃ Br F Me H Br CF₃ Br F Et H Br CF₃ Br F i-Pr HBr CF₃ Br F t-Bu H Br CF₃ Br F Me Me Cl Cl Br F Me H Cl Cl Br F Et H ClCl Br F i-Pr H Cl Cl Br F t-Bu H Cl Cl Br F Me Me Br Cl Br F Me H Br ClBr F Et H Br Cl Br F i-Pr H Br Cl Br F t-Bu H Br Cl Br F Me Me Cl Br BrF Me H Cl Br Br F Et H Cl Br Br F i-Pr H Cl Br Br F t-Bu H Cl Br Br F MeMe Br Br Br F Me H Br Br Br F Et H Br Br Br F i-Pr H Br Br Br F t-Bu HBr Br Br F Me Me Cl OCH₂CF₃ Br F Me H Cl OCH₂CF₃ Br F Et H Cl OCH₂CF₃ BrF i-Pr H Cl OCH₂CF₃ Br F t-Bu H Cl OCH₂CF₃ Br F Me Me Br OCH₂CF₃ Br F MeH Br OCH₂CF₃ Br F Et H Br OCH₂CF₃ Br F i-Pr H Br OCH₂CF₃ Br F t-Bu H BrOCH₂CF₃ Br F Me Me Cl CF₃ Br Cl Me H Cl CF₃ Br Cl Et H Cl CF₃ Br Cl i-PrH Cl CF₃ Br Cl t-Bu H Cl CF₃ Br Cl Me Me Br CF₃ Br Cl Me H Br CF₃ Br ClEt H Br CF₃ Br Cl i-Pr H Br CF₃ Br Cl t-Bu H Br CF₃ Br Cl Me Me Cl Cl BrCl Me H Cl Cl Br Cl Et H Cl Cl Br Cl i-Pr H Cl Cl Br Cl t-Bu H Cl Cl BrCl Me Me Br Cl Br Cl Me H Br Cl Br Cl Et H Br Cl Br Cl i-Pr H Br Cl BrCl t-Bu H Br Cl Br Cl Me Me Cl Br Br Cl Me H Cl Br Br Cl Et H Cl Br BrCl i-Pr H Cl Br Br Cl t-Bu H Cl Br Br Cl Me Me Br Br Br Cl Me H Br Br BrCl Et H Br Br Br Cl i-Pr H Br Br Br Cl t-Bu H Br Br Br Cl Me Me ClOCH₂CF₃ Br Cl Me H Cl OCH₂CF₃ Br Cl Et H Cl OCH₂CF₃ Br Cl i-Pr H ClOCH₂CF₃ Br Cl t-Bu H Cl OCH₂CF₃ Br Cl Me Me Br OCH₂CF₃ Br Cl Me H BrOCH₂CF₃ Br Cl Et H Br OCH₂CF₃ Br Cl i-Pr H Br OCH₂CF₃ Br Cl t-Bu H BrOCH₂CF₃ Br Cl Me Me Cl CF₃ Br Br Me H Cl CF₃ Br Br Et H Cl CF₃ Br Bri-Pr H Cl CF₃ Br Br t-Bu H Cl CF₃ Br Br Me Me Br CF₃ Br Br Me H Br CF₃Br Br Et H Br CF₃ Br Br i-Pr H Br CF₃ Br Br t-Bu H Br CF₃ Br Br Me Me ClCl Br Br Me H Cl Cl Br Br Et H Cl Cl Br Br i-Pr H Cl Cl Br Br t-Bu H ClCl Br Br Me Me Br Cl Br Br Me H Br Cl Br Br Et H Br Cl Br Br i-Pr H BrCl Br Br t-Bu H Br Cl Br Br Me Me Cl Br Br Br Me H Cl Br Br Br Et H ClBr Br Br i-Pr H Cl Br Br Br t-Bu H Cl Br Br Br Me Me Br Br Br Br Me H BrBr Br Br Et H Br Br Br Br i-Pr H Br Br Br Br t-Bu H Br Br Br Br Me Me ClOCH₂CF₃ Br Br Me H Cl OCH₂CF₃ Br Br Et H Cl OCH₂CF₃ Br Br i-Pr H ClOCH₂CF₃ Br Br t-Bu H Cl OCH₂CF₃ Br Br Me Me Br OCH₂CF₃ Br Br Me H BrOCH₂CF₃ Br Br Et H Br OCH₂CF₃ Br Br i-Pr H Br OCH₂CF₃ Br Br t-Bu H BrOCH₂CF₃ Br Br Me Me Cl CF₃ Br I Me H Cl CF₃ Br I Et H Cl CF₃ Br I i-Pr HCl CF₃ Br I t-Bu H Cl CF₃ Br I Me Me Br CF₃ Br I Me H Br CF₃ Br I Et HBr CF₃ Br I i-Pr H Br CF₃ Br I t-Bu H Br CF₃ Br I Me Me Cl Cl Br I Me HCl Cl Br I Et H Cl Cl Br I i-Pr H Cl Cl Br I t-Bu H Cl Cl Br I Me Me BrCl Br I Me H Br Cl Br I Et H Br Cl Br I i-Pr H Br Cl Br I t-Bu H Br ClBr I Me Me Cl Br Br I Me H Cl Br Br I Et H Cl Br Br I i-Pr H Cl Br Br It-Bu H Cl Br Br I Me Me Br Br Br I Me H Br Br Br I Et H Br Br Br I i-PrH Br Br Br I t-Bu H Br Br Br I Me Me Cl OCH₂CF₃ Br I Me H Cl OCH₂CF₃ BrI Et H Cl OCH₂CF₃ Br I i-Pr H Cl OCH₂CF₃ Br I t-Bu H Cl OCH₂CF₃ Br I MeMe Br OCH₂CF₃ Br I Me H Br OCH₂CF₃ Br I Et H Br OCH₂CF₃ Br I i-Pr H BrOCH₂CF₃ Br I t-Bu H Br OCH₂CF₃ Br I Me Me Cl CF₃ Br CF₃ Me H Cl CF₃ BrCF₃ Et H Cl CF₃ Br CF₃ i-Pr H Cl CF₃ Br CF₃ t-Bu H Cl CF₃ Br CF₃ Me MeBr CF₃ Br CF₃ Me H Br CF₃ Br CF₃ Et H Br CF₃ Br CF₃ i-Pr H Br CF₃ Br CF₃t-Bu H Br CF₃ Br CF₃ Me Me Cl Cl Br CF₃ Me H Cl Cl Br CF₃ Et H Cl Cl BrCF₃ i-Pr H Cl Cl Br CF₃ t-Bu H Cl Cl Br CF₃ Me Me Br Cl Br CF₃ Me H BrCl Br CF₃ Et H Br Cl Br CF₃ i-Pr H Br Cl Br CF₃ t-Bu H Br Cl Br CF₃ MeMe Cl Br Br CF₃ Me H Cl Br Br CF₃ Et H Cl Br Br CF₃ i-Pr H Cl Br Br CF₃t-Bu H Cl Br Br CF₃ Me Me Br Br Br CF₃ Me H Br Br Br CF₃ Et H Br Br BrCF₃ i-Pr H Br Br Br CF₃ t-Bu H Br Br Br CF₃ Me Me Cl OCH₂CF₃ Br CF₃ Me HCl OCH₂CF₃ Br CF₃ Et H Cl OCH₂CF₃ Br CF₃ i-Pr H Cl OCH₂CF₃ Br CF₃ t-Bu HCl OCH₂CF₃ Br CF₃ Me Me Br OCH₂CF₃ Br CF₃ Me H Br OCH₂CF₃ Br CF₃ Et H BrOCH₂CF₃ Br CF₃ i-Pr H Br OCH₂CF₃ Br CF₃ t-Bu H Br OCH₂CF₃ Br CF₃ Me Me

[0258] TABLE 6

R⁶(a) R⁵(a) R⁴(a) R⁴(b) R³ R² Cl CF₃ CH₃ H Me H Cl CF₃ CH₃ H Et H Cl CF₃CH₃ H i-Pr H Cl CF₃ CH₃ H t-Bu H Cl CF₃ CH₃ H Me Me Br CF₃ CH₃ H Me H BrCF₃ CH₃ H Et H Br CF₃ CH₃ H i-Pr H Br CF₃ CH₃ H t-Bu H Br CF₃ CH₃ H MeMe Cl Cl CH₃ H Me H Cl Cl CH₃ H Et H Cl Cl CH₃ H i-Pr H Cl Cl CH₃ H t-BuH Cl Cl CH₃ H Me Me Br Cl CH₃ H Me H Br Cl CH₃ H Et H Br Cl CH₃ H i-Pr HBr Cl CH₃ H t-Bu H Br Cl CH₃ H Me Me Cl Br CH₃ H Me H Cl Br CH₃ H Et HCl Br CH₃ H i-Pr H Cl Br CH₃ H t-Bu H Cl Br CH₃ H Me Me Br Br CH₃ H Me HBr Br CH₃ H Et H Br Br CH₃ H i-Pr H Br Br CH₃ H t-Bu H Br Br CH₃ H Me MeCl OCH₂CF₃ CH₃ H Me H Cl OCH₂CF₃ CH₃ H Et H Cl OCH₂CF₃ CH₃ H i-Pr H ClOCH₂CF₃ CH₃ H t-Bu H Cl OCH₂CF₃ CH₃ H Me Me Br OCH₂CF₃ CH₃ H Me H BrOCH₂CF₃ CH₃ H Et H Br OCH₂CF₃ CH₃ H i-Pr H Br OCH₂CF₃ CH₃ H t-Bu H BrOCH₂CF₃ CH₃ H Me Me Cl CF₃ CH₃ F Me H Cl CF₃ CH₃ F Et H Cl CF₃ CH₃ Fi-Pr H Cl CF₃ CH₃ F t-Bu H Cl CF₃ CH₃ F Me Me Br CF₃ CH₃ F Me H Br CF₃CH₃ F Et H Br CF₃ CH₃ F i-Pr H Br CF₃ CH₃ F t-Bu H Br CF₃ CH₃ F Me Me ClCl CH₃ F Me H Cl Cl CH₃ F Et H Cl Cl CH₃ F i-Pr H Cl Cl CH₃ F t-Bu H ClCl CH₃ F Me Me Br Cl CH₃ F Me H Br Cl CH₃ F Et H Br Cl CH₃ F i-Pr H BrCl CH₃ F t-Bu H Br Cl CH₃ F Me Me Cl Br CH₃ F Me H Cl Br CH₃ F Et H ClBr CH₃ F i-Pr H Cl Br CH₃ F t-Bu H Cl Br CH₃ F Me Me Br Br CH₃ F Me H BrBr CH₃ F Et H Br Br CH₃ F i-Pr H Br Br CH₃ F t-Bu H Br Br CH₃ F Me Me ClOCH₂CF₃ CH₃ F Me H Cl OCH₂CF₃ CH₃ F Et H Cl OCH₂CF₃ CH₃ F i-Pr H ClOCH₂CF₃ CH₃ F t-Bu H Cl OCH₂CF₃ CH₃ F Me Me Br OCH₂CF₃ CH₃ F Me H BrOCH₂CF₃ CH₃ F Et H Br OCH₂CF₃ CH₃ F i-Pr H Br OCH₂CF₃ CH₃ F t-Bu H BrOCH₂CF₃ CH₃ F Me Me Cl CF₃ CH₃ Cl Me H Cl CF₃ CH₃ Cl Et H Cl CF₃ CH₃ Cli-Pr H Cl CF₃ CH₃ Cl t-Bu H Cl CF₃ CH₃ Cl Me Me Br CF₃ CH₃ Cl Me H BrCF₃ CH₃ Cl Et H Br CF₃ CH₃ Cl i-Pr H Br CF₃ CH₃ Cl t-Bu H Br CF₃ CH₃ ClMe Me Cl Cl CH₃ Cl Me H Cl Cl CH₃ Cl Et H Cl Cl CH₃ Cl i-Pr H Cl Cl CH₃Cl t-Bu H Cl Cl CH₃ Cl Me Me Br Cl CH₃ Cl Me H Br Cl CH₃ Cl Et H Br ClCH₃ Cl i-Pr H Br Cl CH₃ Cl t-Bu H Br Cl CH₃ Cl Me Me Cl Br CH₃ Cl Me HCl Br CH₃ Cl Et H Cl Br CH₃ Cl i-Pr H Cl Br CH₃ Cl t-Bu H Cl Br CH₃ ClMe Me Br Br CH₃ Cl Me H Br Br CH₃ Cl Et H Br Br CH₃ Cl i-Pr H Br Br CH₃Cl t-Bu H Br Br CH₃ Cl Me Me Cl OCH₂CF₃ CH₃ Cl Me H Cl OCH₂CF₃ CH₃ Cl EtH Cl OCH₂CF₃ CH₃ Cl i-Pr H Cl OCH₂CF₃ CH₃ Cl t-Bu H Cl OCH₂CF₃ CH₃ Cl MeMe Br OCH₂CF₃ CH₃ Cl Me H Br OCH₂CF₃ CH₃ Cl Et H Br OCH₂CF₃ CH₃ Cl i-PrH Br OCH₂CF₃ CH₃ Cl t-Bu H Br OCH₂CF₃ CH₃ Cl Me Me Cl CF₃ CH₃ Br Me H ClCF₃ CH₃ Br Et H Cl CF₃ CH₃ Br i-Pr H Cl CF₃ CH₃ Br t-Bu H Cl CF₃ CH₃ BrMe Me Br CF₃ CH₃ Br Me H Br CF₃ CH₃ Br Et H Br CF₃ CH₃ Br i-Pr H Br CF₃CH₃ Br t-Bu H Br CF₃ CH₃ Br Me Me Cl Cl CH₃ Br Me H Cl Cl CH₃ Br Et H ClCl CH₃ Br i-Pr H Cl Cl CH₃ Br t-Bu H Cl Cl CH₃ Br Me Me Br Cl CH₃ Br MeH Br Cl CH₃ Br Et H Br Cl CH₃ Br i-Pr H Br Cl CH₃ Br t-Bu H Br Cl CH₃ BrMe Me Cl Br CH₃ Br Me H Cl Br CH₃ Br Et H Cl Br CH₃ Br i-Pr H Cl Br CH₃Br t-Bu H Cl Br CH₃ Br Me Me Br Br CH₃ Br Me H Br Br CH₃ Br Et H Br BrCH₃ Br i-Pr H Br Br CH₃ Br t-Bu H Br Br CH₃ Br Me Me Cl OCH₂CF₃ CH₃ BrMe H Cl OCH₂CF₃ CH₃ Br Et H Cl OCH₂CF₃ CH₃ Br i-Pr H Cl OCH₂CF₃ CH₃ Brt-Bu H Cl OCH₂CF₃ CH₃ Br Me Me Br OCH₂CF₃ CH₃ Br Me H Br OCH₂CF₃ CH₃ BrEt H Br OCH₂CF₃ CH₃ Br i-Pr H Br OCH₂CF₃ CH₃ Br t-Bu H Br OCH₂CF₃ CH₃ BrMe Me Cl CF₃ CH₃ I Me H Cl CF₃ CH₃ I Et H Cl CF₃ CH₃ I i-Pr H Cl CF₃ CH₃I t-Bu H Cl CF₃ CH₃ I Me Me Br CF₃ CH₃ I Me H Br CF₃ CH₃ I Et H Br CF₃CH₃ I i-Pr H Br CF₃ CH₃ I t-Bu H Br CF₃ CH₃ I Me Me Cl Cl CH₃ I Me H ClCl CH₃ I Et H Cl Cl CH₃ I i-Pr H Cl Cl CH₃ I t-Bu H Cl Cl CH₃ I Me Me BrCl CH₃ I Me H Br Cl CH₃ I Et H Br Cl CH₃ I i-Pr H Br Cl CH₃ I t-Bu H BrCl CH₃ I Me Me Cl Br CH₃ I Me H Cl Br CH₃ I Et H Cl Br CH₃ I i-Pr H ClBr CH₃ I t-Bu H Cl Br CH₃ I Me Me Br Br CH₃ I Me H Br Br CH₃ I Et H BrBr CH₃ I i-Pr H Br Br CH₃ I t-Bu H Br Br CH₃ I Me Me Cl OCH₂CF₃ CH₃ I MeH Cl OCH₂CF₃ CH₃ I Et H Cl OCH₂CF₃ CH₃ I i-Pr H Cl OCH₂CF₃ CH₃ I t-Bu HCl OCH₂CF₃ CH₃ I Me Me Br OCH₂CF₃ CH₃ I Me H Br OCH₂CF₃ CH₃ I Et H BrOCH₂CF₃ CH₃ I i-Pr H Br OCH₂CF₃ CH₃ I t-Bu H Br OCH₂CF₃ CH₃ I Me Me ClCF₃ CH₃ CF₃ Me H Cl CF₃ CH₃ CF₃ Et H Cl CF₃ CH₃ CF₃ i-Pr H Cl CF₃ CH₃CF₃ t-Bu H Cl CF₃ CH₃ CF₃ Me Me Br CF₃ CH₃ CF₃ Me H Br CF₃ CH₃ CF₃ Et HBr CF₃ CH₃ CF₃ i-Pr H Br CF₃ CH₃ CF₃ t-Bu H Br CF₃ CH₃ CF₃ Me Me Cl ClCH₃ CF₃ Me H Cl Cl CH₃ CF₃ Et H Cl Cl CH₃ CF₃ i-Pr H Cl Cl CH₃ CF₃ t-BuH Cl Cl CH₃ CF₃ Me Me Br Cl CH₃ CF₃ Me H Br Cl CH₃ CF₃ Et H Br Cl CH₃CF₃ i-Pr H Br Cl CH₃ CF₃ t-Bu H Br Cl CH₃ CF₃ Me Me Cl Br CH₃ CF₃ Me HCl Br CH₃ CF₃ Et H Cl Br CH₃ CF₃ i-Pr H Cl Br CH₃ CF₃ t-Bu H Cl Br CH₃CF₃ Me Me Br Br CH₃ CF₃ Me H Br Br CH₃ CF₃ Et H Br Br CH₃ CF₃ i-Pr H BrBr CH₃ CF₃ t-Bu H Br Br CH₃ CF₃ Me Me Cl OCH₂CF₃ CH₃ CF₃ Me H Cl OCH₂CF₃CH₃ CF₃ Et H Cl OCH₂CF₃ CH₃ CF₃ i-Pr H Cl OCH₂CF₃ CH₃ CF₃ t-Bu H ClOCH₂CF₃ CH₃ CF₃ Me Me Br OCH₂CF₃ CH₃ CF₃ Me H Br OCH₂CF₃ CH₃ CF₃ Et H BrOCH₂CF₃ CH₃ CF₃ i-Pr H Br OCH₂CF₃ CH₃ CF₃ t-Bu H Br OCH₂CF₃ CH₃ CF₃ MeMe Cl Cl CH₃ Cl n-Pr H Cl Cl CH₃ Cl n-Bu H Cl Cl CH₃ Cl s-Bu H Cl Cl CH₃Cl i-Bu H Cl Cl CH₃ Cl Et Me Cl CF₃ F H Me H Cl CF₃ F H Et H Cl CF₃ F Hi-Pr H Cl CF₃ F H t-Bu H Cl CF₃ F H Me Me Br CF₃ F H Me H Br CF₃ F H EtH Br CF₃ F H i-Pr H Br CF₃ F H t-Bu H Br CF₃ F H Me Me Cl Cl F H Me H ClCl F H Et H Cl Cl F H i-Pr H Cl Cl F H t-Bu H Cl Cl F H Me Me Br Cl F HMe H Br Cl F H Et H Br Cl F H i-Pr H Br Cl F H t-Bu H Br Cl F H Me Me ClBr F H Me H Cl Br F H Et H Cl Br F H i-Pr H Cl Br F H t-Bu H Cl Br F HMe Me Br Br F H Me H Br Br F H Et H Br Br F H i-Pr H Br Br F H t-Bu H BrBr F H Me Me Cl OCH₂CF₃ F H Me H Cl OCH₂CF₃ F H Et H Cl OCH₂CF₃ F H i-PrH Cl OCH₂CF₃ F H t-Bu H Cl OCH₂CF₃ F H Me Me Br OCH₂CF₃ F H Me H BrOCH₂CF₃ F H Et H Br OCH₂CF₃ F H i-Pr H Br OCH₂CF₃ F H t-Bu H Br OCH₂CF₃F H Me Me Cl CF₃ F F Me H Cl CF₃ F F Et H Cl CF₃ F F i-Pr H Cl CF₃ F Ft-Bu H Cl CF₃ F F Me Me Br CF₃ F F Me H Br CF₃ F F Et H Br CF₃ F F i-PrH Br CF₃ F F t-Bu H Br CF₃ F F Me Me Cl Cl F F Me H Cl Cl F F Et H Cl ClF F i-Pr H Cl Cl F F t-Bu H Cl Cl F F Me Me Br Cl F F Me H Br Cl F F EtH Br Cl F F i-Pr H Br Cl F F t-Bu H Br Cl F F Me Me Cl Br F F Me H Cl BrF F Et H Cl Br F F i-Pr H Cl Br F F t-Bu H Cl Br F F Me Me Br Br F F MeH Br Br F F Et H Br Br F F i-Pr H Br Br F F t-Bu H Br Br F F Me Me ClOCH₂CF₃ F F Me H Cl OCH₂CF₃ F F Et H Cl OCH₂CF₃ F F i-Pr H Cl OCH₂CF₃ FF t-Bu H Cl OCH₂CF₃ F F Me Me Br OCH₂CF₃ F F Me H Br OCH₂CF₃ F F Et H BrOCH₂CF₃ F F i-Pr H Br OCH₂CF₃ F F t-Bu H Br OCH₂CF₃ F F Me Me Cl CF₃ FCl Me H Cl CF₃ F Cl Et H Cl CF₃ F Cl i-Pr H Cl CF₃ F Cl t-Bu H Cl CF₃ FCl Me Me Br CF₃ F Cl Me H Br CF₃ F Cl Et H Br CF₃ F Cl i-Pr H Br CF₃ FCl t-Bu H Br CF₃ F Cl Me Me Cl Cl F Cl Me H Cl Cl F Cl Et H Cl Cl F Cli-Pr H Cl Cl F Cl t-Bu H Cl Cl F Cl Me Me Br Cl F Cl Me H Br Cl F Cl EtH Br Cl F Cl i-Pr H Br Cl F Cl t-Bu H Br Cl F Cl Me Me Cl Br F Cl Me HCl Br F Cl Et H Cl Br F Cl i-Pr H Cl Br F Cl t-Bu H Cl Br F Cl Me Me BrBr F Cl Me H Br Br F Cl Et H Br Br F Cl i-Pr H Br Br F Cl t-Bu H Br Br FCl Me Me Cl OCH₂CF₃ F Cl Me H Cl OCH₂CF₃ F Cl Et H Cl OCH₂CF₃ F Cl i-PrH Cl OCH₂CF₃ F Cl t-Bu H Cl OCH₂CF₃ F Cl Me Me Br OCH₂CF₃ F Cl Me H BrOCH₂CF₃ F Cl Et H Br OCH₂CF₃ F Cl i-Pr H Br OCH₂CF₃ F Cl t-Bu H BrOCH₂CF₃ F Cl Me Me Cl CF₃ F Br Me H Cl CF₃ F Br Et H Cl CF₃ F Br i-Pr HCl CF₃ F Br t-Bu H Cl CF₃ F Br Me Me Br CF₃ F Br Me H Br CF₃ F Br Et HBr CF₃ F Br i-Pr H Br CF₃ F Br t-Bu H Br CF₃ F Br Me Me Cl Cl F Br Me HCl Cl F Br Et H Cl Cl F Br i-Pr H Cl Cl F Br t-Bu H Cl Cl F Br Me Me BrCl F Br Me H Br Cl F Br Et H Br Cl F Br i-Pr H Br Cl F Br t-Bu H Br Cl FBr Me Me Cl Br F Br Me H Cl Br F Br Et H Cl Br F Br i-Pr H Cl Br F Brt-Bu H Cl Br F Br Me Me Br Br F Br Me H Br Br F Br Et H Br Br F Br i-PrH Br Br F Br t-Bu H Br Br F Br Me Me Cl OCH₂CF₃ F Br Me H Cl OCH₂CF₃ FBr Et H Cl OCH₂CF₃ F Br i-Pr H Cl OCH₂CF₃ F Br t-Bu H Cl OCH₂CF₃ F Br MeMe Br OCH₂CF₃ F Br Me H Br OCH₂CF₃ F Br Et H Br OCH₂CF₃ F Br i-Pr H BrOCH₂CF₃ F Br t-Bu H Br OCH₂CF₃ F Br Me Me Cl CF₃ F I Me H Cl CF₃ F I EtH Cl CF₃ F I i-Pr H Cl CF₃ F I t-Bu H Cl CF₃ F I Me Me Br CF₃ F I Me HBr CF₃ F I Et H Br CF₃ F I i-Pr H Br CF₃ F I t-Bu H Br CF₃ F I Me Me ClCl F I Me H Cl Cl F I Et H Cl Cl F I i-Pr H Cl Cl F I t-Bu H Cl Cl F IMe Me Br Cl F I Me H Br Cl F I Et H Br Cl F I i-Pr H Br Cl F I t-Bu H BrCl F I Me Me Cl Br F I Me H Cl Br F I Et H Cl Br F I i-Pr H Cl Br F It-Bu H Cl Br F I Me Me Br Br F I Me H Br Br F I Et H Br Br F I i-Pr H BrBr F I t-Bu H Br Br F I Me Me Cl OCH₂CF₃ F I Me H Cl OCH₂CF₃ F I Et H ClOCH₂CF₃ F I i-Pr H Cl OCH₂CF₃ F I t-Bu H Cl OCH₂CF₃ F I Me Me Br OCH₂CF₃F I Me H Br OCH₂CF₃ F I Et H Br OCH₂CF₃ F I i-Pr H Br OCH₂CF₃ F I t-Bu HBr OCH₂CF₃ F I Me Me Cl CF₃ F CF₃ Me H Cl CF₃ F CF₃ Et H Cl CF₃ F CF₃i-Pr H Cl CF₃ F CF₃ t-Bu H Cl CF₃ F CF₃ Me Me Br CF₃ F CF₃ Me H Br CF₃ FCF₃ Et H Br CF₃ F CF₃ i-Pr H Br CF₃ F CF₃ t-Bu H Br CF₃ F CF₃ Me Me ClCl F CF₃ Me H Cl Cl F CF₃ Et H Cl Cl F CF₃ i-Pr H Cl Cl F CF₃ t-Bu H ClCl F CF₃ Me Me Br Cl F CF₃ Me H Br Cl F CF₃ Et H Br Cl F CF₃ i-Pr H BrCl F CF₃ t-Bu H Br Cl F CF₃ Me Me Cl Br F CF₃ Me H Cl Br F CF₃ Et H ClBr F CF₃ i-Pr H Cl Br F CF₃ t-Bu H Cl Br F CF₃ Me Me Br Br F CF₃ Me H BrBr F CF₃ Et H Br Br F CF₃ i-Pr H Br Br F CF₃ t-Bu H Br Br F CF₃ Me Me ClOCH₂CF₃ F CF₃ Me H Cl OCH₂CF₃ F CF₃ Et H Cl OCH₂CF₃ F CF₃ i-Pr H ClOCH₂CF₃ F CF₃ t-Bu H Cl OCH₂CF₃ F CF₃ Me Me Br OCH₂CF₃ F CF₃ Me H BrOCH₂CF₃ F CF₃ Et H Br OCH₂CF₃ F CF₃ i-Pr H Br OCH₂CF₃ F CF₃ t-Bu H BrOCH₂CF₃ F CF₃ Me Me Cl CF₃ Cl H Me H Cl CF₃ Cl H Et H Cl CF₃ Cl H i-Pr HCl CF₃ Cl H t-Bu H Cl CF₃ Cl H Me Me Br CF₃ Cl H Me H Br CF₃ Cl H Et HBr CF₃ Cl H i-Pr H Br CF₃ Cl H t-Bu H Br CF₃ Cl H Me Me Cl Cl Cl H Me HCl Cl Cl H Et H Cl Cl Cl H i-Pr H Cl Cl Cl H t-Bu H Cl Cl Cl H Me Me BrCl Cl H Me H Br Cl Cl H Et H Br Cl Cl H i-Pr H Br Cl Cl H t-Bu H Br ClCl H Me Me Cl Br Cl H Me H Cl Br Cl H Et H Cl Br Cl H i-Pr H Cl Br Cl Ht-Bu H Cl Br Cl H Me Me Br Br Cl H Me H Br Br Cl H Et H Br Br Cl H i-PrH Br Br Cl H t-Bu H Br Br Cl H Me Me Cl OCH₂CF₃ Cl H Me H Cl OCH₂CF₃ ClH Et H Cl OCH₂CF₃ Cl H i-Pr H Cl OCH₂CF₃ Cl H t-Bu H Cl OCH₂CF₃ Cl H MeMe Br OCH₂CF₃ Cl H Me H Br OCH₂CF₃ Cl H Et H Br OCH₂CF₃ Cl H i-Pr H BrOCH₂CF₃ Cl H t-Bu H Br OCH₂CF₃ Cl H Me Me Cl CF₃ Cl F Me H Cl CF₃ Cl FEt H Cl CF₃ Cl F i-Pr H Cl CF₃ Cl F t-Bu H Cl CF₃ Cl F Me Me Br CF₃ Cl FMe H Br CF₃ Cl F Et H Br CF₃ Cl F i-Pr H Br CF₃ Cl F t-Bu H Br CF₃ Cl FMe Me Cl Cl Cl F Me H Cl Cl Cl F Et H Cl Cl Cl F i-Pr H Cl Cl Cl F t-BuH Cl Cl Cl F Me Me Br Cl Cl F Me H Br Cl Cl F Et H Br Cl Cl F i-Pr H BrCl Cl F t-Bu H Br Cl Cl F Me Me Cl Br Cl F Me H Cl Br Cl F Et H Cl Br ClF i-Pr H Cl Br Cl F t-Bu H Cl Br Cl F Me Me Br Br Cl F Me H Br Br Cl FEt H Br Br Cl F i-Pr H Br Br Cl F t-Bu H Br Br Cl F Me Me Cl OCH₂CF₃ ClF Me H Cl OCH₂CF₃ Cl F Et H Cl OCH₂CF₃ Cl F i-Pr H Cl OCH₂CF₃ Cl F t-BuH Cl OCH₂CF₃ Cl F Me Me Br OCH₂CF₃ Cl F Me H Br OCH₂CF₃ Cl F Et H BrOCH₂CF₃ Cl F i-Pr H Br OCH₂CF₃ Cl F t-Bu H Br OCH₂CF₃ Cl F Me Me Cl CF₃Cl Cl Me H Cl CF₃ Cl Cl Et H Cl CF₃ Cl Cl i-Pr H Cl CF₃ Cl Cl t-Bu H ClCF₃ Cl Cl Me Me Br CF₃ Cl Cl Me H Br CF₃ Cl Cl Et H Br CF₃ Cl Cl i-Pr HBr CF₃ Cl Cl t-Bu H Br CF₃ Cl Cl Me Me Cl Cl Cl Cl Me H Cl Cl Cl Cl Et HCl Cl Cl Cl i-Pr H Cl Cl Cl Cl t-Bu H Cl Cl Cl Cl Me Me Br Cl Cl Cl Me HBr Cl Cl Cl Et H Br Cl Cl Cl i-Pr H Br Cl Cl Cl t-Bu H Br Cl Cl Cl Me MeCl Br Cl Cl Me H Cl Br Cl Cl Et H Cl Br Cl Cl i-Pr H Cl Br Cl Cl t-Bu HCl Br Cl Cl Me Me Br Br Cl Cl Me H Br Br Cl Cl Et H Br Br Cl Cl i-Pr HBr Br Cl Cl t-Bu H Br Br Cl Cl Me Me Cl OCH₂CF₃ Cl Cl Me H Cl OCH₂CF₃ ClCl Et H Cl OCH₂CF₃ Cl Cl i-Pr H Cl OCH₂CF₃ Cl Cl t-Bu H Cl OCH₂CF₃ Cl ClMe Me Br OCH₂CF₃ Cl Cl Me H Br OCH₂CF₃ Cl Cl Et H Br OCH₂CF₃ Cl Cl i-PrH Br OCH₂CF₃ Cl Cl t-Bu H Br OCH₂CF₃ Cl Cl Me Me Cl CF₃ Cl Br Me H ClCF₃ Cl Br Et H Cl CF₃ Cl Br i-Pr H Cl CF₃ Cl Br t-Bu H Cl CF₃ Cl Br MeMe Br CF₃ Cl Br Me H Br CF₃ Cl Br Et H Br CF₃ Cl Br i-Pr H Br CF₃ Cl Brt-Bu H Br CF₃ Cl Br Me Me Cl Cl Cl Br Me H Cl Cl Cl Br Et H Cl Cl Cl Bri-Pr H Cl Cl Cl Br t-Bu H Cl Cl Cl Br Me Me Br Cl Cl Br Me H Br Cl Cl BrEt H Br Cl Cl Br i-Pr H Br Cl Cl Br t-Bu H Br Cl Cl Br Me Me Cl Br Cl BrMe H Cl Br Cl Br Et H Cl Br Cl Br i-Pr H Cl Br Cl Br t-Bu H Cl Br Cl BrMe Me Br Br Cl Br Me H Br Br Cl Br Et H Br Br Cl Br i-Pr H Br Br Cl Brt-Bu H Br Br Cl Br Me Me Cl OCH₂CF₃ Cl Br Me H Cl OCH₂CF₃ Cl Br Et H ClOCH₂CF₃ Cl Br i-Pr H Cl OCH₂CF₃ Cl Br t-Bu H Cl OCH₂CF₃ Cl Br Me Me BrOCH₂CF₃ Cl Br Me H Br OCH₂CF₃ Cl Br Et H Br OCH₂CF₃ Cl Br i-Pr H BrOCH₂CF₃ Cl Br t-Bu H Br OCH₂CF₃ Cl Br Me Me Cl CF₃ Cl I Me H Cl CF₃ Cl IEt H Cl CF₃ Cl I i-Pr H Cl CF₃ Cl I t-Bu H Cl CF₃ Cl I Me Me Br CF₃ Cl IMe H Br CF₃ Cl I Et H Br CF₃ Cl I i-Pr H Br CF₃ Cl I t-Bu H Br CF₃ Cl IMe Me Cl Cl Cl I Me H Cl Cl Cl I Et H Cl Cl Cl I i-Pr H Cl Cl Cl I t-BuH Cl Cl Cl I Me Me Br Cl Cl I Me H Br Cl Cl I Et H Br Cl Cl I i-Pr H BrCl Cl I t-Bu H Br Cl Cl I Me Me Cl Br Cl I Me H Cl Br Cl I Et H Cl Br ClI i-Pr H Cl Br Cl I t-Bu H Cl Br Cl I Me Me Br Br Cl I Me H Br Br Cl IEt H Br Br Cl I i-Pr H Br Br Cl I t-Bu H Br Br Cl I Me Me Cl OCH₂CF₃ ClI Me H Cl OCH₂CF₃ Cl I Et H Cl OCH₂CF₃ Cl I i-Pr H Cl OCH₂CF₃ Cl I t-BuH Cl OCH₂CF₃ Cl I Me Me Br OCH₂CF₃ Cl I Me H Br OCH₂CF₃ Cl I Et H BrOCH₂CF₃ Cl I i-Pr H Br OCH₂CF₃ Cl I t-Bu H Br OCH₂CF₃ Cl I Me Me Cl CF₃Cl CF₃ Me H Cl CF₃ Cl CF₃ Et H Cl CF₃ Cl CF₃ i-Pr H Cl CF₃ Cl CF₃ t-Bu HCl CF₃ Cl CF₃ Me Me Br CF₃ Cl CF₃ Me H Br CF₃ Cl CF₃ Et H Br CF₃ Cl CF₃i-Pr H Br CF₃ Cl CF₃ t-Bu H Br CF₃ Cl CF₃ Me Me Cl Cl Cl CF₃ Me H Cl ClCl CF₃ Et H Cl Cl Cl CF₃ i-Pr H Cl Cl Cl CF₃ t-Bu H Cl Cl Cl CF₃ Me MeBr Cl Cl CF₃ Me H Br Cl Cl CF₃ Et H Br Cl Cl CF₃ i-Pr H Br Cl Cl CF₃t-Bu H Br Cl Cl CF₃ Me Me Cl Br Cl CF₃ Me H Cl Br Cl CF₃ Et H Cl Br ClCF₃ i-Pr H Cl Br Cl CF₃ t-Bu H Cl Br Cl CF₃ Me Me Br Br Cl CF₃ Me H BrBr Cl CF₃ Et H Br Br Cl CF₃ i-Pr H Br Br Cl CF₃ t-Bu H Br Br Cl CF₃ MeMe Cl OCH₂CF₃ Cl CF₃ Me H Cl OCH₂CF₃ Cl CF₃ Et H Cl OCH₂CF₃ Cl CF₃ i-PrH Cl OCH₂CF₃ Cl CF₃ t-Bu H Cl OCH₂CF₃ Cl CF₃ Me Me Br OCH₂CF₃ Cl CF₃ MeH Br OCH₂CF₃ Cl CF₃ Et H Br OCH₂CF₃ Cl CF₃ i-Pr H Br OCH₂CF₃ Cl CF₃ t-BuH Br OCH₂CF₃ Cl CF₃ Me Me Cl Cl Cl Cl n-Pr H Cl Cl Cl Cl n-Bu H Cl Cl ClCl s-Bu H Cl Cl Cl Cl i-Bu H Cl Cl Cl Cl Et Et Cl CF₃ Br H Me H Cl CF₃Br H Et H Cl CF₃ Br H i-Pr H Cl CF₃ Br H t-Bu H Cl CF₃ Br H Me Me Br CF₃Br H Me H Br CF₃ Br H Et H Br CF₃ Br H i-Pr H Br CF₃ Br H t-Bu H Br CF₃Br H Me Me Cl Cl Br H Me H Cl Cl Br H Et H Cl Cl Br H i-Pr H Cl Cl Br Ht-Bu H Cl Cl Br H Me Me Br Cl Br H Me H Br Cl Br H Et H Br Cl Br H i-PrH Br Cl Br H t-Bu H Br Cl Br H Me Me Cl Br Br H Me H Cl Br Br H Et H ClBr Br H i-Pr H Cl Br Br H t-Bu H Cl Br Br H Me Me Br Br Br H Me H Br BrBr H Et H Br Br Br H i-Pr H Br Br Br H t-Bu H Br Br Br H Me Me ClOCH₂CF₃ Br H Me H Cl OCH₂CF₃ Br H Et H Cl OCH₂CF₃ Br H i-Pr H Cl OCH₂CF₃Br H t-Bu H Cl OCH₂CF₃ Br H Me Me Br OCH₂CF₃ Br H Me H Br OCH₂CF₃ Br HEt H Br OCH₂CF₃ Br H i-Pr H Br OCH₂CF₃ Br H t-Bu H Br OCH₂CF₃ Br H Me MeCl CF₃ Br F Me H Cl CF₃ Br F Et H Cl CF₃ Br F i-Pr H Cl CF₃ Br F t-Bu HCl CF₃ Br F Me Me Br CF₃ Br F Me H Br CF₃ Br F Et H Br CF₃ Br F i-Pr HBr CF₃ Br F t-Bu H Br CF₃ Br F Me Me Cl Cl Br F Me H Cl Cl Br F Et H ClCl Br F i-Pr H Cl Cl Br F t-Bu H Cl Cl Br F Me Me Br Cl Br F Me H Br ClBr F Et H Br Cl Br F i-Pr H Br Cl Br F t-Bu H Br Cl Br F Me Me Cl Br BrF Me H Cl Br Br F Et H Cl Br Br F i-Pr H Cl Br Br F t-Bu H Cl Br Br F MeMe Br Br Br F Me H Br Br Br F Et H Br Br Br F i-Pr H Br Br Br F t-Bu HBr Br Br F Me Me Cl OCH₂CF₃ Br F Me H Cl OCH₂CF₃ Br F Et H Cl OCH₂CF₃ BrF i-Pr H Cl OCH₂CF₃ Br F t-Bu H Cl OCH₂CF₃ Br F Me Me Br OCH₂CF₃ Br F MeH Br OCH₂CF₃ Br F Et H Br OCH₂CF₃ Br F i-Pr H Br OCH₂CF₃ Br F t-Bu H BrOCH₂CF₃ Br F Me Me Cl CF₃ Br Cl Me H Cl CF₃ Br Cl Et H Cl CF₃ Br Cl i-PrH Cl CF₃ Br Cl t-Bu H Cl CF₃ Br Cl Me Me Br CF₃ Br Cl Me H Br CF₃ Br ClEt H Br CF₃ Br Cl i-Pr H Br CF₃ Br Cl t-Bu H Br CF₃ Br Cl Me Me Cl Cl BrCl Me H Cl Cl Br Cl Et H Cl Cl Br Cl i-Pr H Cl Cl Br Cl t-Bu H Cl Cl BrCl Me Me Br Cl Br Cl Me H Br Cl Br Cl Et H Br Cl Br Cl i-Pr H Br Cl BrCl t-Bu H Br Cl Br Cl Me Me Cl Br Br Cl Me H Cl Br Br Cl Et H Cl Br BrCl i-Pr H Cl Br Br Cl t-Bu H Cl Br Br Cl Me Me Br Br Br Cl Me H Br Br BrCl Et H Br Br Br Cl i-Pr H Br Br Br Cl t-Bu H Br Br Br Cl Me Me ClOCH₂CF₃ Br Cl Me H Cl OCH₂CF₃ Br Cl Et H Cl OCH₂CF₃ Br Cl i-Pr H ClOCH₂CF₃ Br Cl t-Bu H Cl OCH₂CF₃ Br Cl Me Me Br OCH₂CF₃ Br Cl Me H BrOCH₂CF₃ Br Cl Et H Br OCH₂CF₃ Br Cl i-Pr H Br OCH₂CF₃ Br Cl t-Bu H BrOCH₂CF₃ Br Cl Me Me Cl CF₃ Br Br Me H Cl CF₃ Br Br Et H Cl CF₃ Br Bri-Pr H Cl CF₃ Br Br t-Bu H Cl CF₃ Br Br Me Me Br CF₃ Br Br Me H Br CF₃Br Br Et H Br CF₃ Br Br i-Pr H Br CF₃ Br Br t-Bu H Br CF₃ Br Br Me Me ClCl Br Br Me H Cl Cl Br Br Et H Cl Cl Br Br i-Pr H Cl Cl Br Br t-Bu H ClCl Br Br Me Me Br Cl Br Br Me H Br Cl Br Br Et H Br Cl Br Br i-Pr H BrCl Br Br t-Bu H Br Cl Br Br Me Me Cl Br Br Br Me H Cl Br Br Br Et H ClBr Br Br i-Pr H Cl Br Br Br t-Bu H Cl Br Br Br Me Me Br Br Br Br Me H BrBr Br Br Et H Br Br Br Br i-Pr H Br Br Br Br t-Bu H Br Br Br Br Me Me ClOCH₂CF₃ Br Br Me H Cl OCH₂CF₃ Br Br Et H Cl OCH₂CF₃ Br Br i-Pr H ClOCH₂CF₃ Br Br t-Bu H Cl OCH₂CF₃ Br Br Me Me Br OCH₂CF₃ Br Br Me H BrOCH₂CF₃ Br Br Et H Br OCH₂CF₃ Br Br i-Pr H Br OCH₂CF₃ Br Br t-Bu H BrOCH₂CF₃ Br Br Me Me Cl CF₃ Br I Me H Cl CF₃ Br I Et H Cl CF₃ Br I i-Pr HCl CF₃ Br I t-Bu H Cl CF₃ Br I Me Me Br CF₃ Br I Me H Br CF₃ Br I Et HBr CF₃ Br I i-Pr H Br CF₃ Br I t-Bu H Br CF₃ Br I Me Me Cl Cl Br I Me HCl Cl Br I Et H Cl Cl Br I i-Pr H Cl Cl Br I t-Bu H Cl Cl Br I Me Me BrCl Br I Me H Br Cl Br I Et H Br Cl Br I i-Pr H Br Cl Br I t-Bu H Br ClBr I Me Me Cl Br Br I Me H Cl Br Br I Et H Cl Br Br I i-Pr H Cl Br Br It-Bu H Cl Br Br I Me Me Br Br Br I Me H Br Br Br I Et H Br Br Br I i-PrH Br Br Br I t-Bu H Br Br Br I Me Me Cl OCH₂CF₃ Br I Me H Cl OCH₂CF₃ BrI Et H Cl OCH₂CF₃ Br I i-Pr H Cl OCH₂CF₃ Br I t-Bu H Cl OCH₂CF₃ Br I MeMe Br OCH₂CF₃ Br I Me H Br OCH₂CF₃ Br I Et H Br OCH₂CF₃ Br I i-Pr H BrOCH₂CF₃ Br I t-Bu H Br OCH₂CF₃ Br I Me Me Cl CF₃ Br CF₃ Me H Cl CF₃ BrCF₃ Et H Cl CF₃ Br CF₃ i-Pr H Cl CF₃ Br CF₃ t-Bu H Cl CF₃ Br CF₃ Me MeBr CF₃ Br CF₃ Me H Br CF₃ Br CF₃ Et H Br CF₃ Br CF₃ i-Pr H Br CF₃ Br CF₃t-Bu H Br CF₃ Br CF₃ Me Me Cl Cl Br CF₃ Me H Cl Cl Br CF₃ Et H Cl Cl BrCF₃ i-Pr H Cl Cl Br CF₃ t-Bu H Cl Cl Br CF₃ Me Me Br Cl Br CF₃ Me H BrCl Br CF₃ Et H Br Cl Br CF₃ i-Pr H Br Cl Br CF₃ t-Bu H Br Cl Br CF₃ MeMe Cl Br Br CF₃ Me H Cl Br Br CF₃ Et H Cl Br Br CF₃ i-Pr H Cl Br Br CF₃t-Bu H Cl Br Br CF₃ Me Me Br Br Br CF₃ Me H Br Br Br CF₃ Et H Br Br BrCF₃ i-Pr H Br Br Br CF₃ t-Bu H Br Br Br CF₃ Me Me Cl OCH₂CF₃ Br CF₃ Me HCl OCH₂CF₃ Br CF₃ Et H Cl OCH₂CF₃ Br CF₃ i-Pr H Cl OCH₂CF₃ Br CF₃ t-Bu HCl OCH₂CF₃ Br CF₃ Me Me Br OCH₂CF₃ Br CF₃ Me H Br OCH₂CF₃ Br CF₃ Et H BrOCH₂CF₃ Br CF₃ i-Pr H Br OCH₂CF₃ Br CF₃ t-Bu H Br OCH₂CF₃ Br CF₃ Me Me

[0259] TABLE 7

R⁶(a) R⁵(a) R⁴(a) R⁴(b) R³ R² R⁶(a) R⁵(a) R⁴(a) R⁴(b) R³ R² Cl CF₃ CH₃ HMe H Cl CF₃ Cl H Me H Cl CF₃ CH₃ H Et H Cl CF₃ Cl H Et H Cl CF₃ CH₃ Hi-Pr H Cl CF₃ Cl H i-Pr H Cl CF₃ CH₃ H t-Bu H Cl CF₃ Cl H t-Bu H Cl CF₃CH₃ H Me Me Cl CF₃ Cl H Me Me Br CF₃ CH₃ H Me H Br CF₃ Cl H Me H Br CF₃CH₃ H Et H Br CF₃ Cl H Et H Br CF₃ CH₃ H i-Pr H Br CF₃ Cl H i-Pr H BrCF₃ CH₃ H t-Bu H Br CF₃ Cl H t-Bu H Br CF₃ CH₃ H Me Me Br CF₃ Cl H Me MeCl Cl CH₃ H Me H Cl Cl Cl H Me H Cl Cl CH₃ H Et H Cl Cl Cl H Et H Cl ClCH₃ H i-Pr H Cl Cl Cl H i-Pr H Cl Cl CH₃ H t-Bu H Cl Cl Cl H t-Bu H ClCl CH₃ H Me Me Cl Cl Cl H Me Me Br Cl CH₃ H Me H Br Cl Cl H Me H Br ClCH₃ H Et H Br Cl Cl H Et H Br Cl CH₃ H i-Pr H Br Cl Cl H i-Pr H Br ClCH₃ H t-Bu H Br Cl Cl H t-Bu H Br Cl CH₃ H Me Me Br Cl Cl H Me Me Cl BrCH₃ H Me H Cl Br Cl H Me H Cl Br CH₃ H Et H Cl Br Cl H Et H Cl Br CH₃ Hi-Pr H Cl Br Cl H i-Pr H Cl Br CH₃ H t-Bu H Cl Br Cl H t-Bu H Cl Br CH₃H Me Me Cl Br Cl H Me Me Br Br CH₃ H Me H Br Br Cl H Me H Br Br CH₃ H EtH Br Br Cl H Et H Br Br CH₃ H i-Pr H Br Br Cl H i-Pr H Br Br CH₃ H t-BuH Br Br Cl H t-Bu H Br Br CH₃ H Me Me Br Br Cl H Me Me Cl OCH₂CF₃ CH₃ HMe H Cl OCH₂CF₃ Cl H Me H Cl OCH₂CF₃ CH₃ H Et H Cl OCH₂CF₃ Cl H Et H ClOCH₂CF₃ CH₃ H i-Pr H Cl OCH₂CF₃ Cl H i-Pr H Cl OCH₂CF₃ CH₃ H t-Bu H ClOCH₂CF₃ Cl H t-Bu H Cl OCH₂CF₃ CH₃ H Me Me Cl OCH₂CF₃ Cl H Me Me BrOCH₂CF₃ CH₃ H Me H Br OCH₂CF₃ Cl H Me H Br OCH₂CF₃ CH₃ H Et H Br OCH₂CF₃Cl H Et H Br OCH₂CF₃ CH₃ H i-Pr H Br OCH₂CF₃ Cl H i-Pr H Br OCH₂CF₃ CH₃H t-Bu H Br OCH₂CF₃ Cl H t-Bu H Br OCH₂CF₃ CH₃ H Me Me Br OCH₂CF₃ Cl HMe Me Cl CF₃ CH₃ F Me H Cl CF₃ Cl F Me H Cl CF₃ CH₃ F Et H Cl CF₃ Cl FEt H Cl CF₃ CH₃ F i-Pr H Cl CF₃ Cl F i-Pr H Cl CF₃ CH₃ F t-Bu H Cl CF₃Cl F t-Bu H Cl CF₃ CH₃ F Me Me Cl CF₃ Cl F Me Me Br CF₃ CH₃ F Me H BrCF₃ Cl F Me H Br CF₃ CH₃ F Et H Br CF₃ Cl F Et H Br CF₃ CH₃ F i-Pr H BrCF₃ Cl F i-Pr H Br CF₃ CH₃ F t-Bu H Br CF₃ Cl F t-Bu H Br CF₃ CH₃ F MeMe Br CF₃ Cl F Me Me Cl Cl CH₃ F Me H Cl Cl Cl F Me H Cl Cl CH₃ F Et HCl Cl Cl F Et H Cl Cl CH₃ F i-Pr H Cl Cl Cl F i-Pr H Cl Cl CH₃ F t-Bu HCl Cl Cl F t-Bu H Cl Cl CH₃ F Me Me Cl Cl Cl F Me Me Br Cl CH₃ F Me H BrCl Cl F Me H Br Cl CH₃ F Et H Br Cl Cl F Et H Br Cl CH₃ F i-Pr H Br ClCl F i-Pr H Br Cl CH₃ F t-Bu H Br Cl Cl F t-Bu H Br Cl CH₃ F Me Me Br ClCl F Me Me Cl Br CH₃ F Me H Cl Br Cl F Me H Cl Br CH₃ F Et H Cl Br Cl FFt H Cl Br CH₃ F i-Pr H Cl Br Cl F i-Pr H Cl Br CH₃ F t-Bu H Cl Br Cl Ft-Bu H Cl Br CH₃ F Me Me Cl Br Cl F Me Me Br Br CH₃ F Me H Br Br Cl F MeH Br Br CH₃ F Et H Br Br Cl F Et H Br Br CH₃ F i-Pr H Br Br Cl F i-Pr HBr Br CH₃ F t-Bu H Br Br Cl F t-Bu H Br Br CH₃ F Me Me Br Br Cl F Me MeCl OCH₂CF₃ CH₃ F Me H Cl OCH₂CF₃ Cl F Me H Cl OCH₂CF₃ CH₃ F Et H ClOCH₂CF₃ Cl F Et H Cl OCH₂CF₃ CH₃ F i-Pr H Cl OCH₂CF₃ Cl F i-Pr H ClOCH₂CF₃ CH₃ F t-Bu H Cl OCH₂CF₃ Cl F t-Bu H Cl OCH₂CF₃ CH₃ F Me Me ClOCH₂CF₃ Cl F Me Me Br OCH₂CF₃ CH₃ F Me H Br OCH₂CF₃ Cl F Me H Br OCH₂CF₃CH₃ F Et H Br OCH₂CF₃ Cl F Et H Br OCH₂CF₃ CH₃ F i-Pr H Br OCH₂CF₃ Cl Fi-Pr H Br OCH₂CF₃ CH₃ F t-Bu H Br OCH₂CF₃ Cl F t-Bu H Br OCH₂CF₃ CH₃ FMe Me Br OCH₂CF₃ Cl F Me Me Cl CF₃ CH₃ Cl Me H Cl CF₃ Cl Cl Me H Cl CF₃CH₃ Cl Et H Cl CF₃ Cl Cl Et H Cl CF₃ CH₃ Cl i-Pr H Cl CF₃ Cl Cl i-Pr HCl CF₃ CH₃ Cl t-Bu H Cl CF₃ Cl Cl t-Bu H Cl CF₃ CH₃ Cl Me Me Cl CF₃ ClCl Me Me Br CF₃ CH₃ Cl Me H Br CF₃ Cl Cl Me H Br CF₃ CH₃ Cl Et H Br CF₃Cl Cl Et H Br CF₃ CH₃ Cl i-Pr H Br CF₃ Cl Cl i-Pr H Br CF₃ CH₃ Cl t-Bu HBr CF₃ Cl Cl t-Bu H Br CF₃ CH₃ Cl Me Me Br CF₃ Cl Cl Me Me Cl Cl CH₃ ClMe H Cl Cl Cl Cl Me H Cl Cl CH₃ Cl Et H Cl Cl Cl Cl Et H Cl Cl CH₃ Cli-Pr H Cl Cl Cl Cl i-Pr H Cl Cl CH₃ Cl t-Bu H Cl Cl Cl Cl t-Bu H Cl ClCH₃ Cl Me Me Cl Cl Cl Cl Me Me Br Cl CH₃ Cl Me H Br Cl Cl Cl Me H Br ClCH₃ Cl Et H Br Cl Cl Cl Et H Br Cl CH₃ Cl i-Pr H Br Cl Cl Cl i-Pr H BrCl CH₃ Cl t-Bu H Br Cl Cl Cl t-Bu H Br Cl CH₃ Cl Me Me Br Cl Cl Cl Me MeCl Br CH₃ Cl Me H Cl Br Cl Cl Me H Cl Br CH₃ Cl Et H Cl Br Cl Cl Et H ClBr CH₃ Cl i-Pr H Cl Br Cl Cl i-Pr H Cl Br CH₃ Cl t-Bu H Cl Br Cl Cl t-BuH Cl Br CH₃ Cl Me Me Cl Br Cl Cl Me Me Br Br CH₃ Cl Me H Br Br Cl Cl MeH Br Br CH₃ Cl Et H Br Br Cl Cl Et H Br Br CH₃ Cl i-Pr H Br Br Cl Cli-Pr H Br Br CH₃ Cl t-Bu H Br Br Cl Cl t-Bu H Br Br CH₃ Cl Me Me Br BrCl Cl Me Me Cl OCH₂CF₃ CH₃ Cl Me H Cl OCH₂CF₃ Cl Cl Me H Cl OCH₂CF₃ CH₃Cl Et H Cl OCH₂CF₃ Cl Cl Et H Cl OCH₂CF₃ CH₃ Cl i-Pr H Cl OCH₂CF₃ Cl Cli-Pr H Cl OCH₂CF₃ CH₃ Cl t-Bu H Cl OCH₂CF₃ Cl Cl t-Bu H Cl OCH₂CF₃ CH₃Cl Me Me Cl OCH₂CF₃ Cl Cl Me Me Br OCH₂CF₃ CH₃ Cl Me H Br OCH₂CF₃ Cl ClMe H Br OCH₂CF₃ CH₃ Cl Et H Br OCH₂CF₃ Cl Cl Et H Br OCH₂CF₃ CH₃ Cl i-PrH Br OCH₂CF₃ Cl Cl i-Pr H Br OCH₂CF₃ CH₃ Cl t-Bu H Br OCH₂CF₃ Cl Cl t-BuH Br OCH₂CF₃ CH₃ Cl Me Me Br OCH₂CF₃ Cl Cl Me Me Cl CF₃ CH₃ Br Me H ClCF₃ Cl Br Me H Cl CF₃ CH₃ Br Et H Cl CF₃ Cl Br Et H Cl CF₃ CH₃ Br i-Pr HCl CF₃ Cl Br i-Pr H Cl CF₃ CH₃ Br t-Bu H Cl CF₃ Cl Br t-Bu H Cl CF₃ CH₃Br Me Me Cl CF₃ Cl Br Me Me Br CF₃ CH₃ Br Me H Br CF₃ Cl Br Me H Br CF₃CH₃ Br Et H Br CF₃ Cl Br Et H Br CF₃ CH₃ Br i-Pr H Br CF₃ Cl Br i-Pr HBr CF₃ CH₃ Br t-Bu H Br CF₃ Cl Br t-Bu H Br CF₃ CH₃ Br Me Me Br CF₃ ClBr Me Me Cl Cl CH₃ Br Me H Cl Cl Cl Br Me H Cl Cl CH₃ Br Et H Cl Cl ClBr Et H Cl Cl CH₃ Br i-Pr H Cl Cl Cl Br i-Pr H Cl Cl CH₃ Br t-Bu H Cl ClCl Br t-Bu H Cl Cl CH₃ Br Me Me Cl Cl Cl Br Me Me Br Cl CH₃ Br Me H BrCl Cl Br Me H Br Cl CH₃ Br Et H Br Cl Cl Br Et H Br Cl CH₃ Br i-Pr H BrCl Cl Br i-Pr H Br Cl CH₃ Br t-Bu H Br Cl Cl Br t-Bu H Br Cl CH₃ Br MeMe Br Cl Cl Br Me Me Cl Br CH₃ Br Me H Cl Br Cl Br Me H Cl Br CH₃ Br EtH Cl Br Cl Br Et H Cl Br CH₃ Br i-Pr H Cl Br Cl Br i-Pr H Cl Br CH₃ Brt-Bu H Cl Br Cl Br t-Bu H Cl Br CH₃ Br Me Me Cl Br Cl Br Me Me Br Br CH₃Br Me H Br Br Cl Br Me H Br Br CH₃ Br Et H Br Br Cl Br Et H Br Br CH₃ Bri-Pr H Br Br Cl Br i-Pr H Br Br CH₃ Br t-Bu H Br Br Cl Br t-Bu H Br BrCH₃ Br Me Me Br Br Cl Br Me Me Cl OCH₂CF₃ CH₃ Br Me H Cl OCH₂CF₃ Cl BrMe H Cl OCH₂CF₃ CH₃ Br Et H Cl OCH₂CF₃ Cl Br Et H Cl OCH₂CF₃ CH₃ Br i-PrH Cl OCH₂CF₃ Cl Br i-Pr H Cl OCH₂CF₃ CH₃ Br t-Bu H Cl OCH₂CF₃ Cl Br t-BuH Cl OCH₂CF₃ CH₃ Br Me Me Cl OCH₂CF₃ Cl Br Me Me Br OCH₂CF₃ CH₃ Br Me HBr OCH₂CF₃ Cl Br Me H Br OCH₂CF₃ CH₃ Br Et H Br OCH₂CF₃ Cl Br Et H BrOCH₂CF₃ CH₃ Br i-Pr H Br OCH₂CF₃ Cl Br i-Pr H Br OCH₂CF₃ CH₃ Br t-Bu HBr OCH₂CF₃ Cl Br t-Bu H Br OCH₂CF₃ CH₃ Br Me Me Br OCH₂CF₃ Cl Br Me MeCl CF₃ CH₃ I Me H Cl CF₃ Cl I Me H Cl CF₃ CH₃ I Et H Cl CF₃ Cl I Et H ClCF₃ CH₃ I i-Pr H Cl CF₃ Cl I i-Pr H Cl CF₃ CH₃ I t-Bu H Cl CF₃ Cl I t-BuH Cl CF₃ CH₃ I Me Me Cl CF₃ Cl I Me Me Br CF₃ CH₃ I Me H Br CF₃ Cl I MeH Br CF₃ CH₃ I Et H Br CF₃ Cl I Et H Br CF₃ CH₃ I i-Pr H Br CF₃ Cl Ii-Pr H Br CF₃ CH₃ I t-Bu H Br CF₃ Cl I t-Bu H Br CF₃ CH₃ I Me Me Br CF₃Cl I Me Me Cl Cl CH₃ I Me H Cl Cl Cl I Me H Cl Cl CH₃ I Et H Cl Cl Cl IEt H Cl Cl CH₃ I i-Pr H Cl Cl Cl I i-Pr H Cl Cl CH₃ I t-Bu H Cl Cl Cl It-Bu H Cl Cl CH₃ I Me Me Cl Cl Cl I Me Me Br Cl CH₃ I Me H Br Cl Cl I MeH Br Cl CH₃ I Et H Br Cl Cl I Et H Br Cl CH₃ I i-Pr H Br Cl Cl I i-Pr HBr Cl CH₃ I t-Bu H Br Cl Cl I t-Bu H Br Cl CH₃ I Me Me Br Cl Cl I Me MeCl Br CH₃ I Me H Cl Br Cl I Me H Cl Br CH₃ I Et H Cl Br Cl I Et H Cl BrCH₃ I i-Pr H Cl Br Cl I i-Pr H Cl Br CH₃ I t-Bu H Cl Br Cl I t-Bu H ClBr CH₃ I Me Me Cl Br Cl I Me Me Br Br CH₃ I Me H Br Br Cl I Me H Br BrCH₃ I Et H Br Br Cl I Et H Br Br CH₃ I i-Pr H Br Br Cl I i-Pr H Br BrCH₃ I t-Bu H Br Br Cl I t-Bu H Br Br CH₃ I Me Me Br Br Cl I Me Me ClOCH₂CF₃ CH₃ I Me H Cl OCH₂CF₃ Cl I Me H Cl OCH₂CF₃ CH₃ I Et H Cl OCH₂CF₃Cl I Et H Cl OCH₂CF₃ CH₃ I i-Pr H Cl OCH₂CF₃ Cl I i-Pr H Cl OCH₂CF₃ CH₃I t-Bu H Cl OCH₂CF₃ Cl I t-Bu H Cl OCH₂CF₃ CH₃ I Me Me Cl OCH₂CF₃ Cl IMe Me Br OCH₂CF₃ CH₃ I Me H Br OCH₂CF₃ Cl I Me H Br OCH₂CF₃ CH₃ I Et HBr OCH₂CF₃ Cl I Et H Br OCH₂CF₃ CH₃ I i-Pr H Br OCH₂CF₃ Cl I i-Pr H BrOCH₂CF₃ CH₃ I t-Bu H Br OCH₂CF₃ Cl I t-Bu H Br OCH₂CF₃ CH₃ I Me Me BrOCH₂CF₃ Cl I Me Me Cl CF₃ CH₃ CF₃ Me H Cl CF₃ Cl CF₃ Me H Cl CF₃ CH₃ CF₃Et H Cl CF₃ Cl CF₃ Et H Cl CF₃ CH₃ CF₃ i-Pr H Cl CF₃ Cl CF₃ i-Pr H ClCF₃ CH₃ CF₃ t-Bu H Cl CF₃ Cl CF₃ t-Bu H Cl CF₃ CH₃ CF₃ Me Me Cl CF₃ ClCF₃ Me Me Br CF₃ CH₃ CF₃ Me H Br CF₃ Cl CF₃ Me H Br CF₃ CH₃ CF₃ Et H BrCF₃ Cl CF₃ Et H Br CF₃ CH₃ CF₃ i-Pr H Br CF₃ Cl CF₃ i-Pr H Br CF₃ CH₃CF₃ t-Bu H Br CF₃ Cl CF₃ t-Bu H Br CF₃ CH₃ CF₃ Me Me Br CF₃ Cl CF₃ Me MeCl Cl CH₃ CF₃ Me H Cl Cl Cl CF₃ Me H Cl Cl CH₃ CF₃ Et H Cl Cl Cl CF₃ EtH Cl Cl CH₃ CF₃ i-Pr H Cl Cl Cl CF₃ i-Pr H Cl Cl CH₃ CF₃ t-Bu H Cl Cl ClCF₃ t-Bu H Cl Cl CH₃ CF₃ Me Me Cl Cl Cl CF₃ Me Me Br Cl CH₃ CF₃ Me H BrCl Cl CF₃ Me H Br Cl CH₃ CF₃ Et H Br Cl Cl CF₃ Et H Br Cl CH₃ CF₃ i-Pr HBr Cl Cl CF₃ i-Pr H Br Cl CH₃ CF₃ t-Bu H Br Cl Cl CF₃ t-Bu H Br Cl CH₃CF₃ Me Me Br Cl Cl CF₃ Me Me Cl Br CH₃ CF₃ Me H Cl Br Cl CF₃ Me H Cl BrCH₃ CF₃ Et H Cl Br Cl CF₃ Et H Cl Br CH₃ CF₃ i-Pr H Cl Br Cl CF₃ i-Pr HCl Br CH₃ CF₃ t-Bu H Cl Br Cl CF₃ t-Bu H Cl Br CH₃ CF₃ Me Me Cl Br ClCF₃ Me Me Br Br CH₃ CF₃ Me H Br Br Cl CF₃ Me H Br Br CH₃ CF₃ Et H Br BrCl CF₃ Et H Br Br CH₃ CF₃ i-Pr H Br Br Cl CF₃ i-Pr H Br Br CH₃ CF₃ t-BuH Br Br Cl CF₃ t-Bu H Br Br CH₃ CF₃ Me Me Br Br Cl CF₃ Me Me Cl OCH₂CF₃CH₃ CF₃ Me H Cl OCH₂CF₃ Cl CF₃ Me H Cl OCH₂CF₃ CH₃ CF₃ Et H Cl OCH₂CF₃Cl CF₃ Et H Cl OCH₂CF₃ CH₃ CF₃ i-Pr H Cl OCH₂CF₃ Cl CF₃ i-Pr H ClOCH₂CF₃ CH₃ CF₃ t-Bu H Cl OCH₂CF₃ Cl CF₃ t-Bu H Cl OCH₂CF₃ CH₃ CF₃ Me MeCl OCH₂CF₃ Cl CF₃ Me Me Br OCH₂CF₃ CH₃ CF₃ Me H Br OCH₂CF₃ Cl CF₃ Me HBr OCH₂CF₃ CH₃ CF₃ Et H Br OCH₂CF₃ Cl CF₃ Et H Br OCH₂CF₃ CH₃ CF₃ i-Pr HBr OCH₂CF₃ Cl CF₃ i-Pr H Br OCH₂CF₃ CH₃ CF₃ t-Bu H Br OCH₂CF₃ Cl CF₃t-Bu H Br OCH₂CF₃ CH₃ CF₃ Me Me Br OCH₂CF₃ Cl CF₃ Me Me Cl Cl CH₃ Cln-Pr H Cl Cl Cl Cl n-Pr H Cl Cl CH₃ Cl n-Bu H Cl Cl Cl Cl n-Bu H Cl ClCH₃ Cl s-Bu H Cl Cl Cl Cl s-Bu H Cl Cl CH₃ Cl i-Bu H Cl Cl Cl Cl i-Bu HCl Cl CH₃ Cl Et Me Cl Cl Cl Cl Et Et Cl CF₃ F H Me H Cl CF₃ Br H Me H ClCF₃ F H Et H Cl CF₃ Br H Et H Cl CF₃ F H i-Pr H Cl CF₃ Br H i-Pr H ClCF₃ F H t-Bu H Cl CF₃ Br H t-Bu H Cl CF₃ F H Me Me Cl CF₃ Br H Me Me BrCF₃ F H Me H Br CF₃ Br H Me H Br CF₃ F H Et H Br CF₃ Br H Et H Br CF₃ FH i-Pr H Br CF₃ Br H i-Pr H Br CF₃ F H t-Bu H Br CF₃ Br H t-Bu H Br CF₃F H Me Me Br CF₃ Br H Me Me Cl Cl F H Me H Cl Cl Br H Me H Cl Cl F H EtH Cl Cl Br H Et H Cl Cl F H i-Pr H Cl Cl Br H i-Pr H Cl Cl F H t-Bu H ClCl Br H t-Bu H Cl Cl F H Me Me Cl Cl Br H Me Me Br Cl F H Me H Br Cl BrH Me H Br Cl F H Et H Br Cl Br H Et H Br Cl F H i-Pr H Br Cl Br H i-Pr HBr Cl F H t-Bu H Br Cl Br H t-Bu H Br Cl F H Me Me Br Cl Br H Me Me ClBr F H Me H Cl Br Br H Me H Cl Br F H Et H Cl Br Br H Et H Cl Br F Hi-Pr H Cl Br Br H i-Pr H Cl Br F H t-Bu H Cl Br Br H t-Bu H Cl Br F H MeMe Cl Br Br H Me Me Br Br F H Me H Br Br Br H Me H Br Br F H Et H Br BrBr H Et H Br Br F H i-Pr H Br Br Br H i-Pr H Br Br F H t-Bu H Br Br Br Ht-Bu H Br Br F H Me Me Br Br Br H Me Me Cl OCH₂CF₃ F H Me H Cl OCH₂CF₃Br H Me H Cl OCH₂CF₃ F H Et H Cl OCH₂CF₃ Br H Et H Cl OCH₂CF₃ F H i-Pr HCl OCH₂CF₃ Br H i-Pr H Cl OCH₂CF₃ F H t-Bu H Cl OCH₂CF₃ Br H t-Bu H ClOCH₂CF₃ F H Me Me Cl OCH₂CF₃ Br H Me Me Br OCH₂CF₃ F H Me H Br OCH₂CF₃Br H Me H Br OCH₂CF₃ F H Et H Br OCH₂CF₃ Br H Et H Br OCH₂CF₃ F H i-Pr HBr OCH₂CF₃ Br H i-Pr H Br OCH₂CF₃ F H t-Bu H Br OCH₂CF₃ Br H t-Bu H BrOCH₂CF₃ F H Me Me Br OCH₂CF₃ Br H Me Me Cl CF₃ F F Me H Cl CF₃ Br F Me HCl CF₃ F F Et H Cl CF₃ Br F Et H Cl CF₃ F F i-Pr H Cl CF₃ Br F i-Pr H ClCF₃ F F t-Bu H Cl CF₃ Br F t-Bu H Cl CF₃ F F Me Me Cl CF₃ Br F Me Me BrCF₃ F F Me H Br CF₃ Br F Me H Br CF₃ F F Et H Br CF₃ Br F Et H Br CF₃ FF i-Pr H Br CF₃ Br F i-Pr H Br CF₃ F F t-Bu H Br CF₃ Br F t-Bu H Br CF₃F F Me Me Br CF₃ Br F Me Me Cl Cl F F Me H Cl Cl Br F Me H Cl Cl F F EtH Cl Cl Br F Et H Cl Cl F F i-Pr H Cl Cl Br F i-Pr H Cl Cl F F t-Bu H ClCl Br F t-Bu H Cl Cl F F Me Me Cl Cl Br F Me Me Br Cl F F Me H Br Cl BrF Me H Br Cl F F Et H Br Cl Br F Et H Br Cl F F i-Pr H Br Cl Br F i-Pr HBr Cl F F t-Bu H Br Cl Br F t-Bu H Br Cl F F Me Me Br Cl Br F Me Me ClBr F F Me H Cl Br Br F Me H Cl Br F F Et H Cl Br Br F Et H Cl Br F Fi-Pr H Cl Br Br F i-Pr H Cl Br F F t-Bu H Cl Br Br F t-Bu H Cl Br F F MeMe Cl Br Br F Me Me Br Br F F Me H Br Br Br F Me H Br Br F F Et H Br BrBr F Et H Br Br F F i-Pr H Br Br Br F i-Pr H Br Br F F t-Bu H Br Br Br Ft-Bu H Br Br F F Me Me Br Br Br F Me Me Cl OCH₂CF₃ F F Me H Cl OCH₂CF₃Br F Me H Cl OCH₂CF₃ F F Et H Cl OCH₂CF₃ Br F Et H Cl OCH₂CF₃ F F i-Pr HCl OCH₂CF₃ Br F i-Pr H Cl OCH₂CF₃ F F t-Bu H Cl OCH₂CF₃ Br F t-Bu H ClOCH₂CF₃ F F Me Me Cl OCH₂CF₃ Br F Me Me Br OCH₂CF₃ F F Me H Br OCH₂CF₃Br F Me H Br OCH₂CF₃ F F Et H Br OCH₂CF₃ Br F Et H Br OCH₂CF₃ F F i-Pr HBr OCH₂CF₃ Br F i-Pr H Br OCH₂CF₃ F F t-Bu H Br OCH₂CF₃ Br F t-Bu H BrOCH₂CF₃ F F Me Me Br OCH₂CF₃ Br F Me Me Cl CF₃ F Cl Me H Cl CF₃ Br Cl MeH Cl CF₃ F Cl Et H Cl CF₃ Br Cl Et H Cl CF₃ F Cl i-Pr H Cl CF₃ Br Cli-Pr H Cl CF₃ F Cl t-Bu H Cl CF₃ Br Cl t-Bu H Cl CF₃ F Cl Me Me Cl CF₃Br Cl Me Me Br CF₃ F Cl Me H Br CF₃ Br Cl Me H Br CF₃ F Cl Et H Br CF₃Br Cl Et H Br CF₃ F Cl i-Pr H Br CF₃ Br Cl i-Pr H Br CF₃ F Cl t-Bu H BrCF₃ Br Cl t-Bu H Br CF₃ F Cl Me Me Br CF₃ Br Cl Me Me Cl Cl F Cl Me H ClCl Br Cl Me H Cl Cl F Cl Et H Cl Cl Br Cl Et H Cl Cl F Cl i-Pr H Cl ClBr Cl i-Pr H Cl Cl F Cl t-Bu H Cl Cl Br Cl t-Bu H Cl Cl F Cl Me Me Cl ClBr Cl Me Me Br Cl F Cl Me H Br Cl Br Cl Me H Br Cl F Cl Et H Br Cl Br ClEt H Br Cl F Cl i-Pr H Br Cl Br Cl i-Pr H Br Cl F Cl t-Bu H Br Cl Br Clt-Bu H Br Cl F Cl Me Me Br Cl Br Cl Me Me Cl Br F Cl Me H Cl Br Br Cl MeH Cl Br F Cl Et H Cl Br Br Cl Et H Cl Br F Cl i-Pr H Cl Br Br Cl i-Pr HCl Br F Cl t-Bu H Cl Br Br Cl t-Bu H Cl Br F Cl Me Me Cl Br Br Cl Me MeBr Br F Cl Me H Br Br Br Cl Me H Br Br F Cl Et H Br Br Br Cl Et H Br BrF Cl i-Pr H Br Br Br Cl i-Pr H Br Br F Cl t-Bu H Br Br Br Cl t-Bu H BrBr F Cl Me Me Br Br Br Cl Me Me Cl OCH₂CF₃ F Cl Me H Cl OCH₂CF₃ Br Cl MeH Cl OCH₂CF₃ F Cl Et H Cl OCH₂CF₃ Br Cl Et H Cl OCH₂CF₃ F Cl i-Pr H ClOCH₂CF₃ Br Cl i-Pr H Cl OCH₂CF₃ F Cl t-Bu H Cl OCH₂CF₃ Br Cl t-Bu H ClOCH₂CF₃ F Cl Me Me Cl OCH₂CF₃ Br Cl Me Me Br OCH₂CF₃ F Cl Me H BrOCH₂CF₃ Br Cl Me H Br OCH₂CF₃ F Cl Et H Br OCH₂CF₃ Br Cl Et H Br OCH₂CF₃F Cl i-Pr H Br OCH₂CF₃ Br Cl i-Pr H Br OCH₂CF₃ F Cl t-Bu H Br OCH₂CF₃ BrCl t-Bu H Br OCH₂CF₃ F Cl Me Me Br OCH₂CF₃ Br Cl Me Me Cl CF₃ F Br Me HCl CF₃ Br Br Me H Cl CF₃ F Br Et H Cl CF₃ Br Br Et H Cl CF₃ F Br i-Pr HCl CF₃ Br Br i-Pr H Cl CF₃ F Br t-Bu H Cl CF₃ Br Br t-Bu H Cl CF₃ F BrMe Me Cl CF₃ Br Br Me Me Br CF₃ F Br Me H Br CF₃ Br Br Me H Br CF₃ F BrEt H Br CF₃ Br Br Et H Br CF₃ F Br i-Pr H Br CF₃ Br Br i-Pr H Br CF₃ FBr t-Bu H Br CF₃ Br Br t-Bu H Br CF₃ F Br Me Me Br CF₃ Br Br Me Me Cl ClF Br Me H Cl Cl Br Br Me H Cl Cl F Br Et H Cl Cl Br Br Et H Cl Cl F Bri-Pr H Cl Cl Br Br i-Pr H Cl Cl F Br t-Bu H Cl Cl Br Br t-Bu H Cl Cl FBr Me Me Cl Cl Br Br Me Me Br Cl F Br Me H Br Cl Br Br Me H Br Cl F BrEt H Br Cl Br Br Et H Br Cl F Br i-Pr H Br Cl Br Br i-Pr H Br Cl F Brt-Bu H Br Cl Br Br t-Bu H Br Cl F Br Me Me Br Cl Br Br Me Me Cl Br F BrMe H Cl Br Br Br Me H Cl Br F Br Et H Cl Br Br Br Et H Cl Br F Br i-Pr HCl Br Br Br i-Pr H Cl Br F Br t-Bu H Cl Br Br Br t-Bu H Cl Br F Br Me MeCl Br Br Br Me Me Br Br F Br Me H Br Br Br Br Me H Br Br F Br Et H Br BrBr Br Et H Br Br F Br i-Pr H Br Br Br Br i-Pr H Br Br F Br t-Bu H Br BrBr Br t-Bu H Br Br F Br Me Me Br Br Br Br Me Me Cl OCH₂CF₃ F Br Me H ClOCH₂CF₃ Br Br Me H Cl OCH₂CF₃ F Br Et H Cl OCH₂CF₃ Br Br Et H Cl OCH₂CF₃F Br i-Pr H Cl OCH₂CF₃ Br Br i-Pr H Cl OCH₂CF₃ F Br t-Bu H Cl OCH₂CF₃ BrBr t-Bu H Cl OCH₂CF₃ F Br Me Me Cl OCH₂CF₃ Br Br Me Me Br OCH₂CF₃ F BrMe H Br OCH₂CF₃ Br Br Me H Br OCH₂CF₃ F Br Et H Br OCH₂CF₃ Br Br Et H BrOCH₂CF₃ F Br i-Pr H Br OCH₂CF₃ Br Br i-Pr H Br OCH₂CF₃ F Br t-Bu H BrOCH₂CF₃ Br Br t-Bu H Br OCH₂CF₃ F Br Me Me Br OCH₂CF₃ Br Br Me Me Cl CF₃F I Me H Cl CF3 Br I Me H Cl CF₃ F I Et H Cl CF3 Br I Et H Cl CF₃ F Ii-Pr H Cl CF3 Br I i-Pr H Cl CF₃ F I t-Bu H Cl CF3 Br I t-Bu H Cl CF₃ FI Me Me Cl CF3 Br I Me Me Br CF₃ F I Me H Br CF3 Br I Me H Br CF₃ F I EtH Br CF3 Br I Et H Br CF₃ F I i-Pr H Br CF3 Br I i-Pr H Br CF₃ F I t-BuH Br CF3 Br I t-Bu H Br CF₃ F I Me Me Br CF3 Br I Me Me Cl Cl F I Me HCl Cl Br I Me H Cl Cl F I Et H Cl Cl Br I Et H Cl Cl F I i-Pr H Cl Cl BrI i-Pr H Cl Cl F I t-Bu H Cl Cl Br I t-Bu H Cl Cl F I Me Me Cl Cl Br IMe Me Br Cl F I Me H Br Cl Br I Me H Br Cl F I Et H Br Cl Br I Et H BrCl F I i-Pr H Br Cl Br I i-Pr H Br Cl F I t-Bu H Br Cl Br I t-Bu H Br ClF I Me Me Br Cl Br I Me Me Cl Br F I Me H Cl Br Br I Me H Cl Br F I Et HCl Br Br I Et H Cl Br F I i-Pr H Cl Br Br I i-Pr H Cl Br F I t-Bu H ClBr Br 1 t-Bu H Cl Br F I Me Me Cl Br Br I Me Me Br Br F I Me H Br Br BrI Me H Br Br F I Et H Br Br Br I Et H Br Br F I i-Pr H Br Br Br I i-Pr HBr Br F I t-Bu H Br Br Br I t-Bu H Br Br F I Me Me Br Br Br I Me Me ClOCH₂CF₃ F I Me H Cl OCH₂CF₃ Br I Me H Cl OCH₂CF₃ F I Et H Cl OCH₂CF₃ BrI Et H Cl OCH₂CF₃ F I i-Pr H Cl OCH₂CF₃ Br I i-Pr H Cl OCH₂CF₃ F I t-BuH Cl OCH₂CF₃ Br I t-Bu H Cl OCH₂CF₃ F I Me Me Cl OCH₂CF₃ Br I Me Me BrOCH₂CF₃ F I Me H Br OCH₂CF₃ Br I Me H Br OCH₂CF₃ F I Et H Br OCH₂CF₃ BrI Et H Br OCH₂CF₃ F I i-Pr H Br OCH₂CF₃ Br I i-Pr H Br OCH₂CF₃ F I t-BuH Br OCH₂CF₃ Br I t-Bu H Br OCH₂CF₃ F I Me Me Br OCH₂CF₃ Br I Me Me ClCF₃ F CF₃ Me H Cl CF₃ Br CF₃ Me H Cl CF₃ F CF₃ Et H Cl CF₃ Br CF₃ Et HCl CF₃ F CF₃ i-Pr H Cl CF₃ Br CF₃ i-Pr H Cl CF₃ F CF₃ t-Bu H Cl CF₃ BrCF₃ t-Bu H Cl CF₃ F CF₃ Me Me Cl CF₃ Br CF₃ Me Me Br CF₃ F CF₃ Me H BrCF₃ Br CF₃ Me H Br CF₃ F CF₃ Et H Br CF₃ Br CF₃ Et H Br CF₃ F CF₃ i-Pr HBr CF₃ Br CF₃ i-Pr H Br CF₃ F CF₃ t-Bu H Br CF₃ Br CF₃ t-Bu H Br CF₃ FCF₃ Me Me Br CF₃ Br CF₃ Me Me Cl Cl F CF₃ Me H Cl Cl Br CF₃ Me H Cl Cl FCF₃ Et H Cl Cl Br CF₃ Et H Cl Cl F CF₃ i-Pr H Cl Cl Br CF₃ i-Pr H Cl ClF CF₃ t-Bu H Cl Cl Br CF₃ t-Bu H Cl Cl F CF₃ Me Me Cl Cl Br CF₃ Me Me BrCl F CF₃ Me H Br Cl Br CF₃ Me H Br Cl F CF₃ Et H Br Cl Br CF₃ Et H Br ClF CF₃ i-Pr H Br Cl Br CF₃ i-Pr H Br Cl F CF₃ t-Bu H Br Cl Br CF₃ t-Bu HBr Cl F CF₃ Me Me Br Cl Br CF₃ Me Me Cl Br F CF₃ Me H Cl Br Br CF₃ Me HCl Br F CF₃ Et H Cl Br Br CF₃ Et H Cl Br F CF₃ i-Pr H Cl Br Br CF₃ i-PrH Cl Br F CF₃ t-Bu H Cl Br Br CF₃ t-Bu H Cl Br F CF₃ Me Me Cl Br Br CF₃Me Me Br Br F CF₃ Me H Br Br Br CF₃ Me H Br Br F CF₃ Et H Br Br Br CF₃Et H Br Br F CF₃ i-Pr H Br Br Br CF₃ i-Pr H Br Br F CF₃ t-Bu H Br Br BrCF₃ t-Bu H Br Br F CF₃ Me Me Br Br Br CF₃ Me Me Cl OCH₂CF₃ F CF3 Me H ClOCH₂CF₃ Br CF3 Me H Cl OCH₂CF₃ F CF3 Et H Cl OCH₂CF₃ Br CF3 Et H ClOCH₂CF₃ F CF3 i-Pr H Cl OCH₂CF₃ Br CF3 i-Pr H Cl OCH₂CF₃ F CF3 t-Bu H ClOCH₂CF₃ Br CF3 t-Bu H Cl OCH₂CF₃ F CF3 Me Me Cl OCH₂CF₃ Br CF3 Me Me BrOCH₂CF₃ F CF3 Me H Br OCH₂CF₃ Br CF3 Me H Br OCH₂CF₃ F CF3 Et H BrOCH₂CF₃ Br CF3 Et H Br OCH₂CF₃ F CF3 i-Pr H Br OCH₂CF₃ Br CF3 i-Pr H BrOCH₂CF₃ F CF3 t-Bu H Br OCH₂CF₃ Br CF3 t-Bu H Br OCH₂CF₃ F CF3 Me Me BrOCH₂CF₃ Br CF3 Me Me

[0260] TABLE 8

R⁶(a) R⁵(a) R⁴(a) R⁴(b) R³ R² R⁶(a) R⁵(a) R⁴(a) R⁴(b) R³ R² Cl CF₃ CH₃ HMe H Cl CF₃ Cl H Me H Cl CF₃ CH₃ H Et H Cl CF₃ Cl H Et H Cl CF₃ CH₃ Hi-Pr H Cl CF₃ Cl H i-Pr H Cl CF₃ CH₃ H t-Bu H Cl CF₃ Cl H t-Bu H Cl CF₃CH₃ H Me Me Cl CF₃ Cl H Me Me Br CF₃ CH₃ H Me H Br CF₃ Cl H Me H Br CF₃CH₃ H Et H Br CF₃ Cl H Et H Br CF₃ CH₃ H i-Pr H Br CF₃ Cl H i-Pr H BrCF₃ CH₃ H t-Bu H Br CF₃ Cl H t-Bu H Br CF₃ CH₃ H Me Me Br CF₃ Cl H Me MeCl Cl CH₃ H Me H Cl Cl Cl H Me H Cl Cl CH₃ H Et H Cl Cl Cl H Et H Cl ClCH₃ H i-Pr H Cl Cl Cl H i-Pr H Cl Cl CH₃ H t-Bu H Cl Cl Cl H t-Bu H ClCl CH₃ H Me Me Cl Cl Cl H Me Me Br Cl CH₃ H Me H Br Cl Cl H Me H Br ClCH₃ H Et H Br Cl Cl H Et H Br Cl CH₃ H i-Pr H Br Cl Cl H i-Pr H Br ClCH₃ H t-Bu H Br Cl Cl H t-Bu H Br Cl CH₃ H Me Me Br Cl Cl H Me Me Cl BrCH₃ H Me H Cl Br Cl H Me H Cl Br CH₃ H Et H Cl Br Cl H Et H Cl Br CH₃ Hi-Pr H Cl Br Cl H i-Pr H Cl Br CH₃ H t-Bu H Cl Br Cl H t-Bu H Cl Br CH₃H Me Me Cl Br Cl H Me Me Br Br CH₃ H Me H Br Br Cl H Me H Br Br CH₃ H EtH Br Br Cl H Et H Br Br CH₃ H i-Pr H Br Br Cl H i-Pr H Br Br CH₃ H t-BuH Br Br Cl H t-Bu H Br Br CH₃ H Me Me Br Br Cl H Me Me Cl OCH₂CF₃ CH₃ HMe H Cl OCH₂CF₃ Cl H Me H Cl OCH₂CF₃ CH₃ H Et H Cl OCH₂CF₃ Cl H Et H ClOCH₂CF₃ CH₃ H i-Pr H Cl OCH₂CF₃ Cl H i-Pr H Cl OCH₂CF₃ CH₃ H t-Bu H ClOCH₂CF₃ Cl H t-Bu H Cl OCH₂CF₃ CH₃ H Me Me Cl OCH₂CF₃ Cl H Me Me BrOCH₂CF₃ CH₃ H Me H Br OCH₂CF₃ Cl H Me H Br OCH₂CF₃ CH₃ H Et H Br OCH₂CF₃Cl H Et H Br OCH₂CF₃ CH₃ H i-Pr H Br OCH₂CF₃ Cl H i-Pr H Br OCH₂CF₃ CH₃H t-Bu H Br OCH₂CF₃ Cl H t-Bu H Br OCH₂CF₃ CH₃ H Me Me Br OCH₂CF₃ Cl HMe Me Cl CF₃ CH₃ F Me H Cl CF₃ Cl F Me H Cl CF₃ CH₃ F Et H Cl CF₃ Cl FEt H Cl CF₃ CH₃ F i-Pr H Cl CF₃ Cl F i-Pr H Cl CF₃ CH₃ F t-Bu H Cl CF₃Cl F t-Bu H Cl CF₃ CH₃ F Me Me Cl CF₃ Cl F Me Me Br CF₃ CH₃ F Me H BrCF₃ Cl F Me H Br CF₃ CH₃ F Et H Br CF₃ Cl F Et H Br CF₃ CH₃ F i-Pr H BrCF₃ Cl F i-Pr H Br CF₃ CH₃ F t-Bu H Br CF₃ Cl F t-Bu H Br CF₃ CH₃ F MeMe Br CF₃ Cl F Me Me Cl Cl CH₃ F Me H Cl Cl Cl F Me H Cl Cl CH₃ F Et HCl Cl Cl F Et H Cl Cl CH₃ F i-Pr H Cl Cl Cl F i-Pr H Cl Cl CH₃ F t-Bu HCl Cl Cl F t-Bu H Cl Cl CH₃ F Me Me Cl Cl Cl F Me Me Br Cl CH₃ F Me H BrCl Cl F Me H Br Cl CH₃ F Et H Br Cl Cl F Et H Br Cl CH₃ F i-Pr H Br ClCl F i-Pr H Br Cl CH₃ F t-Bu H Br Cl Cl F t-Bu H Br Cl CH₃ F Me Me Br ClCl F Me Me Cl Br CH₃ F Me H Cl Br Cl F Me H Cl Br CH₃ F Et H Cl Br Cl FFt H Cl Br CH₃ F i-Pr H Cl Br Cl F i-Pr H Cl Br CH₃ F t-Bu H Cl Br Cl Ft-Bu H Cl Br CH₃ F Me Me Cl Br Cl F Me Me Br Br CH₃ F Me H Br Br Cl F MeH Br Br CH₃ F Et H Br Br Cl F Et H Br Br CH₃ F i-Pr H Br Br Cl F i-Pr HBr Br CH₃ F t-Bu H Br Br Cl F t-Bu H Br Br CH₃ F Me Me Br Br Cl F Me MeCl OCH₂CF₃ CH₃ F Me H Cl OCH₂CF₃ Cl F Me H Cl OCH₂CF₃ CH₃ F Et H ClOCH₂CF₃ Cl F Et H Cl OCH₂CF₃ CH₃ F i-Pr H Cl OCH₂CF₃ Cl F i-Pr H ClOCH₂CF₃ CH₃ F t-Bu H Cl OCH₂CF₃ Cl F t-Bu H Cl OCH₂CF₃ CH₃ F Me Me ClOCH₂CF₃ Cl F Me Me Br OCH₂CF₃ CH₃ F Me H Br OCH₂CF₃ Cl F Me H Br OCH₂CF₃CH₃ F Et H Br OCH₂CF₃ Cl F Et H Br OCH₂CF₃ CH₃ F i-Pr H Br OCH₂CF₃ Cl Fi-Pr H Br OCH₂CF₃ CH₃ F t-Bu H Br OCH₂CF₃ Cl F t-Bu H Br OCH₂CF₃ CH₃ FMe Me Br OCH₂CF₃ Cl F Me Me Cl CF₃ CH₃ Cl Me H Cl CF₃ Cl Cl Me H Cl CF₃CH₃ Cl Et H Cl CF₃ Cl Cl Et H Cl CF₃ CH₃ Cl i-Pr H Cl CF₃ Cl Cl i-Pr HCl CF₃ CH₃ Cl t-Bu H Cl CF₃ Cl Cl t-Bu H Cl CF₃ CH₃ Cl Me Me Cl CF₃ ClCl Me Me Br CF₃ CH₃ Cl Me H Br CF₃ Cl Cl Me H Br CF₃ CH₃ Cl Et H Br CF₃Cl Cl Et H Br CF₃ CH₃ Cl i-Pr H Br CF₃ Cl Cl i-Pr H Br CF₃ CH₃ Cl t-Bu HBr CF₃ Cl Cl t-Bu H Br CF₃ CH₃ Cl Me Me Br CF₃ Cl Cl Me Me Cl Cl CH₃ ClMe H Cl Cl Cl Cl Me H Cl Cl CH₃ Cl Et H Cl Cl Cl Cl Et H Cl Cl CH₃ Cli-Pr H Cl Cl Cl Cl i-Pr H Cl Cl CH₃ Cl t-Bu H Cl Cl Cl Cl t-Bu H Cl ClCH₃ Cl Me Me Cl Cl Cl Cl Me Me Br Cl CH₃ Cl Me H Br Cl Cl Cl Me H Br ClCH₃ Cl Et H Br Cl Cl Cl Et H Br Cl CH₃ Cl i-Pr H Br Cl Cl Cl i-Pr H BrCl CH₃ Cl t-Bu H Br Cl Cl Cl t-Bu H Br Cl CH₃ Cl Me Me Br Cl Cl Cl Me MeCl Br CH₃ Cl Me H Cl Br Cl Cl Me H Cl Br CH₃ Cl Et H Cl Br Cl Cl Et H ClBr CH₃ Cl i-Pr H Cl Br Cl Cl i-Pr H Cl Br CH₃ Cl t-Bu H Cl Br Cl Cl t-BuH Cl Br CH₃ Cl Me Me Cl Br Cl Cl Me Me Br Br CH₃ Cl Me H Br Br Cl Cl MeH Br Br CH₃ Cl Et H Br Br Cl Cl Et H Br Br CH₃ Cl i-Pr H Br Br Cl Cli-Pr H Br Br CH₃ Cl t-Bu H Br Br Cl Cl t-Bu H Br Br CH₃ Cl Me Me Br BrCl Cl Me Me Cl OCH₂CF₃ CH₃ Cl Me H Cl OCH₂CF₃ Cl Cl Me H Cl OCH₂CF₃ CH₃Cl Et H Cl OCH₂CF₃ Cl Cl Et H Cl OCH₂CF₃ CH₃ Cl i-Pr H Cl OCH₂CF₃ Cl Cli-Pr H Cl OCH₂CF₃ CH₃ Cl t-Bu H Cl OCH₂CF₃ Cl Cl t-Bu H Cl OCH₂CF₃ CH₃Cl Me Me Cl OCH₂CF₃ Cl Cl Me Me Br OCH₂CF₃ CH₃ Cl Me H Br OCH₂CF₃ Cl ClMe H Br OCH₂CF₃ CH₃ Cl Et H Br OCH₂CF₃ Cl Cl Et H Br OCH₂CF₃ CH₃ Cl i-PrH Br OCH₂CF₃ Cl Cl i-Pr H Br OCH₂CF₃ CH₃ Cl t-Bu H Br OCH₂CF₃ Cl Cl t-BuH Br OCH₂CF₃ CH₃ Cl Me Me Br OCH₂CF₃ Cl Cl Me Me Cl CF₃ CH₃ Br Me H ClCF₃ Cl Br Me H Cl CF₃ CH₃ Br Et H Cl CF₃ Cl Br Et H Cl CF₃ CH₃ Br i-Pr HCl CF₃ Cl Br i-Pr H Cl CF₃ CH₃ Br t-Bu H Cl CF₃ Cl Br t-Bu H Cl CF₃ CH₃Br Me Me Cl CF₃ Cl Br Me Me Br CF₃ CH₃ Br Me H Br CF₃ Cl Br Me H Br CF₃CH₃ Br Et H Br CF₃ Cl Br Et H Br CF₃ CH₃ Br i-Pr H Br CF₃ Cl Br i-Pr HBr CF₃ CH₃ Br t-Bu H Br CF₃ Cl Br t-Bu H Br CF₃ CH₃ Br Me Me Br CF₃ ClBr Me Me Cl Cl CH₃ Br Me H Cl Cl Cl Br Me H Cl Cl CH₃ Br Et H Cl Cl ClBr Et H Cl Cl CH₃ Br i-Pr H Cl Cl Cl Br i-Pr H Cl Cl CH₃ Br t-Bu H Cl ClCl Br t-Bu H Cl Cl CH₃ Br Me Me Cl Cl Cl Br Me Me Br Cl CH₃ Br Me H BrCl Cl Br Me H Br Cl CH₃ Br Et H Br Cl Cl Br Et H Br Cl CH₃ Br i-Pr H BrCl Cl Br i-Pr H Br Cl CH₃ Br t-Bu H Br Cl Cl Br t-Bu H Br Cl CH₃ Br MeMe Br Cl Cl Br Me Me Cl Br CH₃ Br Me H Cl Br Cl Br Me H Cl Br CH₃ Br EtH Cl Br Cl Br Et H Cl Br CH₃ Br i-Pr H Cl Br Cl Br i-Pr H Cl Br CH₃ Brt-Bu H Cl Br Cl Br t-Bu H Cl Br CH₃ Br Me Me Cl Br Cl Br Me Me Br Br CH₃Br Me H Br Br Cl Br Me H Br Br CH₃ Br Et H Br Br Cl Br Et H Br Br CH₃ Bri-Pr H Br Br Cl Br i-Pr H Br Br CH₃ Br t-Bu H Br Br Cl Br t-Bu H Br BrCH₃ Br Me Me Br Br Cl Br Me Me Cl OCH₂CF₃ CH₃ Br Me H Cl OCH₂CF₃ Cl BrMe H Cl OCH₂CF₃ CH₃ Br Et H Cl OCH₂CF₃ Cl Br Et H Cl OCH₂CF₃ CH₃ Br i-PrH Cl OCH₂CF₃ Cl Br i-Pr H Cl OCH₂CF₃ CH₃ Br t-Bu H Cl OCH₂CF₃ Cl Br t-BuH Cl OCH₂CF₃ CH₃ Br Me Me Cl OCH₂CF₃ Cl Br Me Me Br OCH₂CF₃ CH₃ Br Me HBr OCH₂CF₃ Cl Br Me H Br OCH₂CF₃ CH₃ Br Et H Br OCH₂CF₃ Cl Br Et H BrOCH₂CF₃ CH₃ Br i-Pr H Br OCH₂CF₃ Cl Br i-Pr H Br OCH₂CF₃ CH₃ Br t-Bu HBr OCH₂CF₃ Cl Br t-Bu H Br OCH₂CF₃ CH₃ Br Me Me Br OCH₂CF₃ Cl Br Me MeCl CF₃ CH₃ I Me H Cl CF₃ Cl I Me H Cl CF₃ CH₃ I Et H Cl CF₃ Cl I Et H ClCF₃ CH₃ I i-Pr H Cl CF₃ Cl I i-Pr H Cl CF₃ CH₃ I t-Bu H Cl CF₃ Cl I t-BuH Cl CF₃ CH₃ I Me Me Cl CF₃ Cl I Me Me Br CF₃ CH₃ I Me H Br CF₃ Cl I MeH Br CF₃ CH₃ I Et H Br CF₃ Cl I Et H Br CF₃ CH₃ I i-Pr H Br CF₃ Cl Ii-Pr H Br CF₃ CH₃ I t-Bu H Br CF₃ Cl I t-Bu H Br CF₃ CH₃ I Me Me Br CF₃Cl I Me Me Cl Cl CH₃ I Me H Cl Cl Cl I Me H Cl Cl CH₃ I Et H Cl Cl Cl IEt H Cl Cl CH₃ I i-Pr H Cl Cl Cl I i-Pr H Cl Cl CH₃ I t-Bu H Cl Cl Cl It-Bu H Cl Cl CH₃ I Me Me Cl Cl Cl I Me Me Br Cl CH₃ I Me H Br Cl Cl I MeH Br Cl CH₃ I Et H Br Cl Cl I Et H Br Cl CH₃ I i-Pr H Br Cl Cl I i-Pr HBr Cl CH₃ I t-Bu H Br Cl Cl I t-Bu H Br Cl CH₃ I Me Me Br Cl Cl I Me MeCl Br CH₃ I Me H Cl Br Cl I Me H Cl Br CH₃ I Et H Cl Br Cl I Et H Cl BrCH₃ I i-Pr H Cl Br Cl I i-Pr H Cl Br CH₃ I t-Bu H Cl Br Cl I t-Bu H ClBr CH₃ I Me Me Cl Br Cl I Me Me Br Br CH₃ I Me H Br Br Cl I Me H Br BrCH₃ I Et H Br Br Cl I Et H Br Br CH₃ I i-Pr H Br Br Cl I i-Pr H Br BrCH₃ I t-Bu H Br Br Cl I t-Bu H Br Br CH₃ I Me Me Br Br Cl I Me Me ClOCH₂CF₃ CH₃ I Me H Cl OCH₂CF₃ Cl I Me H Cl OCH₂CF₃ CH₃ I Et H Cl OCH₂CF₃Cl I Et H Cl OCH₂CF₃ CH₃ I i-Pr H Cl OCH₂CF₃ Cl I i-Pr H Cl OCH₂CF₃ CH₃I t-Bu H Cl OCH₂CF₃ Cl I t-Bu H Cl OCH₂CF₃ CH₃ I Me Me Cl OCH₂CF₃ Cl IMe Me Br OCH₂CF₃ CH₃ I Me H Br OCH₂CF₃ Cl I Me H Br OCH₂CF₃ CH₃ I Et HBr OCH₂CF₃ Cl I Et H Br OCH₂CF₃ CH₃ I i-Pr H Br OCH₂CF₃ Cl I i-Pr H BrOCH₂CF₃ CH₃ I t-Bu H Br OCH₂CF₃ Cl I t-Bu H Br OCH₂CF₃ CH₃ I Me Me BrOCH₂CF₃ Cl I Me Me Cl CF₃ CH₃ CF₃ Me H Cl CF₃ Cl CF₃ Me H Cl CF₃ CH₃ CF₃Et H Cl CF₃ Cl CF₃ Et H Cl CF₃ CH₃ CF₃ i-Pr H Cl CF₃ Cl CF₃ i-Pr H ClCF₃ CH₃ CF₃ t-Bu H Cl CF₃ Cl CF₃ t-Bu H Cl CF₃ CH₃ CF₃ Me Me Cl CF₃ ClCF₃ Me Me Br CF₃ CH₃ CF₃ Me H Br CF₃ Cl CF₃ Me H Br CF₃ CH₃ CF₃ Et H BrCF₃ Cl CF₃ Et H Br CF₃ CH₃ CF₃ i-Pr H Br CF₃ Cl CF₃ i-Pr H Br CF₃ CH₃CF₃ t-Bu H Br CF₃ Cl CF₃ t-Bu H Br CF₃ CH₃ CF₃ Me Me Br CF₃ Cl CF₃ Me MeCl Cl CH₃ CF₃ Me H Cl Cl Cl CF₃ Me H Cl Cl CH₃ CF₃ Et H Cl Cl Cl CF₃ EtH Cl Cl CH₃ CF₃ i-Pr H Cl Cl Cl CF₃ i-Pr H Cl Cl CH₃ CF₃ t-Bu H Cl Cl ClCF₃ t-Bu H Cl Cl CH₃ CF₃ Me Me Cl Cl Cl CF₃ Me Me Br Cl CH₃ CF₃ Me H BrCl Cl CF₃ Me H Br Cl CH₃ CF₃ Et H Br Cl Cl CF₃ Et H Br Cl CH₃ CF₃ i-Pr HBr Cl Cl CF₃ i-Pr H Br Cl CH₃ CF₃ t-Bu H Br Cl Cl CF₃ t-Bu H Br Cl CH₃CF₃ Me Me Br Cl Cl CF₃ Me Me Cl Br CH₃ CF₃ Me H Cl Br Cl CF₃ Me H Cl BrCH₃ CF₃ Et H Cl Br Cl CF₃ Et H Cl Br CH₃ CF₃ i-Pr H Cl Br Cl CF₃ i-Pr HCl Br CH₃ CF₃ t-Bu H Cl Br Cl CF₃ t-Bu H Cl Br CH₃ CF₃ Me Me Cl Br ClCF₃ Me Me Br Br CH₃ CF₃ Me H Br Br Cl CF₃ Me H Br Br CH₃ CF₃ Et H Br BrCl CF₃ Et H Br Br CH₃ CF₃ i-Pr H Br Br Cl CF₃ i-Pr H Br Br CH₃ CF₃ t-BuH Br Br Cl CF₃ t-Bu H Br Br CH₃ CF₃ Me Me Br Br Cl CF₃ Me Me Cl OCH₂CF₃CH₃ CF₃ Me H Cl OCH₂CF₃ Cl CF₃ Me H Cl OCH₂CF₃ CH₃ CF₃ Et H Cl OCH₂CF₃Cl CF₃ Et H Cl OCH₂CF₃ CH₃ CF₃ i-Pr H Cl OCH₂CF₃ Cl CF₃ i-Pr H ClOCH₂CF₃ CH₃ CF₃ t-Bu H Cl OCH₂CF₃ Cl CF₃ t-Bu H Cl OCH₂CF₃ CH₃ CF₃ Me MeCl OCH₂CF₃ Cl CF₃ Me Me Br OCH₂CF₃ CH₃ CF₃ Me H Br OCH₂CF₃ Cl CF₃ Me HBr OCH₂CF₃ CH₃ CF₃ Et H Br OCH₂CF₃ Cl CF₃ Et H Br OCH₂CF₃ CH₃ CF₃ i-Pr HBr OCH₂CF₃ Cl CF₃ i-Pr H Br OCH₂CF₃ CH₃ CF₃ t-Bu H Br OCH₂CF₃ Cl CF₃t-Bu H Br OCH₂CF₃ CH₃ CF₃ Me Me Br OCH₂CF₃ Cl CF₃ Me Me Cl Cl CH₃ Cln-Pr H Cl Cl Cl Cl n-Pr H Cl Cl CH₃ Cl n-Bu H Cl Cl Cl Cl n-Bu H Cl ClCH₃ Cl s-Bu H Cl Cl Cl Cl s-Bu H Cl Cl CH₃ Cl i-Bu H Cl Cl Cl Cl i-Bu HCl Cl CH₃ Cl Et Me Cl Cl Cl Cl Et Et Cl CF₃ F H Me H Cl CF₃ Br H Me H ClCF₃ F H Et H Cl CF₃ Br H Et H Cl CF₃ F H i-Pr H Cl CF₃ Br H i-Pr H ClCF₃ F H t-Bu H Cl CF₃ Br H t-Bu H Cl CF₃ F H Me Me Cl CF₃ Br H Me Me BrCF₃ F H Me H Br CF₃ Br H Me H Br CF₃ F H Et H Br CF₃ Br H Et H Br CF₃ FH i-Pr H Br CF₃ Br H i-Pr H Br CF₃ F H t-Bu H Br CF₃ Br H t-Bu H Br CF₃F H Me Me Br CF₃ Br H Me Me Cl Cl F H Me H Cl Cl Br H Me H Cl Cl F H EtH Cl Cl Br H Et H Cl Cl F H i-Pr H Cl Cl Br H i-Pr H Cl Cl F H t-Bu H ClCl Br H t-Bu H Cl Cl F H Me Me Cl Cl Br H Me Me Br Cl F H Me H Br Cl BrH Me H Br Cl F H Et H Br Cl Br H Et H Br Cl F H i-Pr H Br Cl Br H i-Pr HBr Cl F H t-Bu H Br Cl Br H t-Bu H Br Cl F H Me Me Br Cl Br H Me Me ClBr F H Me H Cl Br Br H Me H Cl Br F H Et H Cl Br Br H Et H Cl Br F Hi-Pr H Cl Br Br H i-Pr H Cl Br F H t-Bu H Cl Br Br H t-Bu H Cl Br F H MeMe Cl Br Br H Me Me Br Br F H Me H Br Br Br H Me H Br Br F H Et H Br BrBr H Et H Br Br F H i-Pr H Br Br Br H i-Pr H Br Br F H t-Bu H Br Br Br Ht-Bu H Br Br F H Me Me Br Br Br H Me Me Cl OCH₂CF₃ F H Me H Cl OCH₂CF₃Br H Me H Cl OCH₂CF₃ F H Et H Cl OCH₂CF₃ Br H Et H Cl OCH₂CF₃ F H i-Pr HCl OCH₂CF₃ Br H i-Pr H Cl OCH₂CF₃ F H t-Bu H Cl OCH₂CF₃ Br H t-Bu H ClOCH₂CF₃ F H Me Me Cl OCH₂CF₃ Br H Me Me Br OCH₂CF₃ F H Me H Br OCH₂CF₃Br H Me H Br OCH₂CF₃ F H Et H Br OCH₂CF₃ Br H Et H Br OCH₂CF₃ F H i-Pr HBr OCH₂CF₃ Br H i-Pr H Br OCH₂CF₃ F H t-Bu H Br OCH₂CF₃ Br H t-Bu H BrOCH₂CF₃ F H Me Me Br OCH₂CF₃ Br H Me Me Cl CF₃ F F Me H Cl CF₃ Br F Me HCl CF₃ F F Et H Cl CF₃ Br F Et H Cl CF₃ F F i-Pr H Cl CF₃ Br F i-Pr H ClCF₃ F F t-Bu H Cl CF₃ Br F t-Bu H Cl CF₃ F F Me Me Cl CF₃ Br F Me Me BrCF₃ F F Me H Br CF₃ Br F Me H Br CF₃ F F Et H Br CF₃ Br F Et H Br CF₃ FF i-Pr H Br CF₃ Br F i-Pr H Br CF₃ F F t-Bu H Br CF₃ Br F t-Bu H Br CF₃F F Me Me Br CF₃ Br F Me Me Cl Cl F F Me H Cl Cl Br F Me H Cl Cl F F EtH Cl Cl Br F Et H Cl Cl F F i-Pr H Cl Cl Br F i-Pr H Cl Cl F F t-Bu H ClCl Br F t-Bu H Cl Cl F F Me Me Cl Cl Br F Me Me Br Cl F F Me H Br Cl BrF Me H Br Cl F F Et H Br Cl Br F Et H Br Cl F F i-Pr H Br Cl Br F i-Pr HBr Cl F F t-Bu H Br Cl Br F t-Bu H Br Cl F F Me Me Br Cl Br F Me Me ClBr F F Me H Cl Br Br F Me H Cl Br F F Et H Cl Br Br F Et H Cl Br F Fi-Pr H Cl Br Br F i-Pr H Cl Br F F t-Bu H Cl Br Br F t-Bu H Cl Br F F MeMe Cl Br Br F Me Me Br Br F F Me H Br Br Br F Me H Br Br F F Et H Br BrBr F Et H Br Br F F i-Pr H Br Br Br F i-Pr H Br Br F F t-Bu H Br Br Br Ft-Bu H Br Br F F Me Me Br Br Br F Me Me Cl OCH₂CF₃ F F Me H Cl OCH₂CF₃Br F Me H Cl OCH₂CF₃ F F Et H Cl OCH₂CF₃ Br F Et H Cl OCH₂CF₃ F F i-Pr HCl OCH₂CF₃ Br F i-Pr H Cl OCH₂CF₃ F F t-Bu H Cl OCH₂CF₃ Br F t-Bu H ClOCH₂CF₃ F F Me Me Cl OCH₂CF₃ Br F Me Me Br OCH₂CF₃ F F Me H Br OCH₂CF₃Br F Me H Br OCH₂CF₃ F F Et H Br OCH₂CF₃ Br F Et H Br OCH₂CF₃ F F i-Pr HBr OCH₂CF₃ Br F i-Pr H Br OCH₂CF₃ F F t-Bu H Br OCH₂CF₃ Br F t-Bu H BrOCH₂CF₃ F F Me Me Br OCH₂CF₃ Br F Me Me Cl CF₃ F Cl Me H Cl CF₃ Br Cl MeH Cl CF₃ F Cl Et H Cl CF₃ Br Cl Et H Cl CF₃ F Cl i-Pr H Cl CF₃ Br Cli-Pr H Cl CF₃ F Cl t-Bu H Cl CF₃ Br Cl t-Bu H Cl CF₃ F Cl Me Me Cl CF₃Br Cl Me Me Br CF₃ F Cl Me H Br CF₃ Br Cl Me H Br CF₃ F Cl Et H Br CF₃Br Cl Et H Br CF₃ F Cl i-Pr H Br CF₃ Br Cl i-Pr H Br CF₃ F Cl t-Bu H BrCF₃ Br Cl t-Bu H Br CF₃ F Cl Me Me Br CF₃ Br Cl Me Me Cl Cl F Cl Me H ClCl Br Cl Me H Cl Cl F Cl Et H Cl Cl Br Cl Et H Cl Cl F Cl i-Pr H Cl ClBr Cl i-Pr H Cl Cl F Cl t-Bu H Cl Cl Br Cl t-Bu H Cl Cl F Cl Me Me Cl ClBr Cl Me Me Br Cl F Cl Me H Br Cl Br Cl Me H Br Cl F Cl Et H Br Cl Br ClEt H Br Cl F Cl i-Pr H Br Cl Br Cl i-Pr H Br Cl F Cl t-Bu H Br Cl Br Clt-Bu H Br Cl F Cl Me Me Br Cl Br Cl Me Me Cl Br F Cl Me H Cl Br Br Cl MeH Cl Br F Cl Et H Cl Br Br Cl Et H Cl Br F Cl i-Pr H Cl Br Br Cl i-Pr HCl Br F Cl t-Bu H Cl Br Br Cl t-Bu H Cl Br F Cl Me Me Cl Br Br Cl Me MeBr Br F Cl Me H Br Br Br Cl Me H Br Br F Cl Et H Br Br Br Cl Et H Br BrF Cl i-Pr H Br Br Br Cl i-Pr H Br Br F Cl t-Bu H Br Br Br Cl t-Bu H BrBr F Cl Me Me Br Br Br Cl Me Me Cl OCH₂CF₃ F Cl Me H Cl OCH₂CF₃ Br Cl MeH Cl OCH₂CF₃ F Cl Et H Cl OCH₂CF₃ Br Cl Et H Cl OCH₂CF₃ F Cl i-Pr H ClOCH₂CF₃ Br Cl i-Pr H Cl OCH₂CF₃ F Cl t-Bu H Cl OCH₂CF₃ Br Cl t-Bu H ClOCH₂CF₃ F Cl Me Me Cl OCH₂CF₃ Br Cl Me Me Br OCH₂CF₃ F Cl Me H BrOCH₂CF₃ Br Cl Me H Br OCH₂CF₃ F Cl Et H Br OCH₂CF₃ Br Cl Et H Br OCH₂CF₃F Cl i-Pr H Br OCH₂CF₃ Br Cl i-Pr H Br OCH₂CF₃ F Cl t-Bu H Br OCH₂CF₃ BrCl t-Bu H Br OCH₂CF₃ F Cl Me Me Br OCH₂CF₃ Br Cl Me Me Cl CF₃ F Br Me HCl CF₃ Br Br Me H Cl CF₃ F Br Et H Cl CF₃ Br Br Et H Cl CF₃ F Br i-Pr HCl CF₃ Br Br i-Pr H Cl CF₃ F Br t-Bu H Cl CF₃ Br Br t-Bu H Cl CF₃ F BrMe Me Cl CF₃ Br Br Me Me Br CF₃ F Br Me H Br CF₃ Br Br Me H Br CF₃ F BrEt H Br CF₃ Br Br Et H Br CF₃ F Br i-Pr H Br CF₃ Br Br i-Pr H Br CF₃ FBr t-Bu H Br CF₃ Br Br t-Bu H Br CF₃ F Br Me Me Br CF₃ Br Br Me Me Cl ClF Br Me H Cl Cl Br Br Me H Cl Cl F Br Et H Cl Cl Br Br Et H Cl Cl F Bri-Pr H Cl Cl Br Br i-Pr H Cl Cl F Br t-Bu H Cl Cl Br Br t-Bu H Cl Cl FBr Me Me Cl Cl Br Br Me Me Br Cl F Br Me H Br Cl Br Br Me H Br Cl F BrEt H Br Cl Br Br Et H Br Cl F Br i-Pr H Br Cl Br Br i-Pr H Br Cl F Brt-Bu H Br Cl Br Br t-Bu H Br Cl F Br Me Me Br Cl Br Br Me Me Cl Br F BrMe H Cl Br Br Br Me H Cl Br F Br Et H Cl Br Br Br Et H Cl Br F Br i-Pr HCl Br Br Br i-Pr H Cl Br F Br t-Bu H Cl Br Br Br t-Bu H Cl Br F Br Me MeCl Br Br Br Me Me Br Br F Br Me H Br Br Br Br Me H Br Br F Br Et H Br BrBr Br Et H Br Br F Br i-Pr H Br Br Br Br i-Pr H Br Br F Br t-Bu H Br BrBr Br t-Bu H Br Br F Br Me Me Br Br Br Br Me Me Cl OCH₂CF₃ F Br Me H ClOCH₂CF₃ Br Br Me H Cl OCH₂CF₃ F Br Et H Cl OCH₂CF₃ Br Br Et H Cl OCH₂CF₃F Br i-Pr H Cl OCH₂CF₃ Br Br i-Pr H Cl OCH₂CF₃ F Br t-Bu H Cl OCH₂CF₃ BrBr t-Bu H Cl OCH₂CF₃ F Br Me Me Cl OCH₂CF₃ Br Br Me Me Br OCH₂CF₃ F BrMe H Br OCH₂CF₃ Br Br Me H Br OCH₂CF₃ F Br Et H Br OCH₂CF₃ Br Br Et H BrOCH₂CF₃ F Br i-Pr H Br OCH₂CF₃ Br Br i-Pr H Br OCH₂CF₃ F Br t-Bu H BrOCH₂CF₃ Br Br t-Bu H Br OCH₂CF₃ F Br Me Me Br OCH₂CF₃ Br Br Me Me Cl CF₃F I Me H Cl CF3 Br I Me H Cl CF₃ F I Et H Cl CF3 Br I Et H Cl CF₃ F Ii-Pr H Cl CF3 Br I i-Pr H Cl CF₃ F I t-Bu H Cl CF3 Br I t-Bu H Cl CF₃ FI Me Me Cl CF3 Br I Me Me Br CF₃ F I Me H Br CF3 Br I Me H Br CF₃ F I EtH Br CF3 Br I Et H Br CF₃ F I i-Pr H Br CF3 Br I i-Pr H Br CF₃ F I t-BuH Br CF3 Br I t-Bu H Br CF₃ F I Me Me Br CF3 Br I Me Me Cl Cl F I Me HCl Cl Br I Me H Cl Cl F I Et H Cl Cl Br I Et H Cl Cl F I i-Pr H Cl Cl BrI i-Pr H Cl Cl F I t-Bu H Cl Cl Br I t-Bu H Cl Cl F I Me Me Cl Cl Br IMe Me Br Cl F I Me H Br Cl Br I Me H Br Cl F I Et H Br Cl Br I Et H BrCl F I i-Pr H Br Cl Br I i-Pr H Br Cl F I t-Bu H Br Cl Br I t-Bu H Br ClF I Me Me Br Cl Br I Me Me Cl Br F I Me H Cl Br Br I Me H Cl Br F I Et HCl Br Br I Et H Cl Br F I i-Pr H Cl Br Br I i-Pr H Cl Br F I t-Bu H ClBr Br 1 t-Bu H Cl Br F I Me Me Cl Br Br I Me Me Br Br F I Me H Br Br BrI Me H Br Br F I Et H Br Br Br I Et H Br Br F I i-Pr H Br Br Br I i-Pr HBr Br F I t-Bu H Br Br Br I t-Bu H Br Br F I Me Me Br Br Br I Me Me ClOCH₂CF₃ F I Me H Cl OCH₂CF₃ Br I Me H Cl OCH₂CF₃ F I Et H Cl OCH₂CF₃ BrI Et H Cl OCH₂CF₃ F I i-Pr H Cl OCH₂CF₃ Br I i-Pr H Cl OCH₂CF₃ F I t-BuH Cl OCH₂CF₃ Br I t-Bu H Cl OCH₂CF₃ F I Me Me Cl OCH₂CF₃ Br I Me Me BrOCH₂CF₃ F I Me H Br OCH₂CF₃ Br I Me H Br OCH₂CF₃ F I Et H Br OCH₂CF₃ BrI Et H Br OCH₂CF₃ F I i-Pr H Br OCH₂CF₃ Br I i-Pr H Br OCH₂CF₃ F I t-BuH Br OCH₂CF₃ Br I t-Bu H Br OCH₂CF₃ F I Me Me Br OCH₂CF₃ Br I Me Me ClCF₃ F CF₃ Me H Cl CF₃ Br CF₃ Me H Cl CF₃ F CF₃ Et H Cl CF₃ Br CF₃ Et HCl CF₃ F CF₃ i-Pr H Cl CF₃ Br CF₃ i-Pr H Cl CF₃ F CF₃ t-Bu H Cl CF₃ BrCF₃ t-Bu H Cl CF₃ F CF₃ Me Me Cl CF₃ Br CF₃ Me Me Br CF₃ F CF₃ Me H BrCF₃ Br CF₃ Me H Br CF₃ F CF₃ Et H Br CF₃ Br CF₃ Et H Br CF₃ F CF₃ i-Pr HBr CF₃ Br CF₃ i-Pr H Br CF₃ F CF₃ t-Bu H Br CF₃ Br CF₃ t-Bu H Br CF₃ FCF₃ Me Me Br CF₃ Br CF₃ Me Me Cl Cl F CF₃ Me H Cl Cl Br CF₃ Me H Cl Cl FCF₃ Et H Cl Cl Br CF₃ Et H Cl Cl F CF₃ i-Pr H Cl Cl Br CF₃ i-Pr H Cl ClF CF₃ t-Bu H Cl Cl Br CF₃ t-Bu H Cl Cl F CF₃ Me Me Cl Cl Br CF₃ Me Me BrCl F CF₃ Me H Br Cl Br CF₃ Me H Br Cl F CF₃ Et H Br Cl Br CF₃ Et H Br ClF CF₃ i-Pr H Br Cl Br CF₃ i-Pr H Br Cl F CF₃ t-Bu H Br Cl Br CF₃ t-Bu HBr Cl F CF₃ Me Me Br Cl Br CF₃ Me Me Cl Br F CF₃ Me H Cl Br Br CF₃ Me HCl Br F CF₃ Et H Cl Br Br CF₃ Et H Cl Br F CF₃ i-Pr H Cl Br Br CF₃ i-PrH Cl Br F CF₃ t-Bu H Cl Br Br CF₃ t-Bu H Cl Br F CF₃ Me Me Cl Br Br CF₃Me Me Br Br F CF₃ Me H Br Br Br CF₃ Me H Br Br F CF₃ Et H Br Br Br CF₃Et H Br Br F CF₃ i-Pr H Br Br Br CF₃ i-Pr H Br Br F CF₃ t-Bu H Br Br BrCF₃ t-Bu H Br Br F CF₃ Me Me Br Br Br CF₃ Me Me Cl OCH₂CF₃ F CF3 Me H ClOCH₂CF₃ Br CF3 Me H Cl OCH₂CF₃ F CF3 Et H Cl OCH₂CF₃ Br CF3 Et H ClOCH₂CF₃ F CF3 i-Pr H Cl OCH₂CF₃ Br CF3 i-Pr H Cl OCH₂CF₃ F CF3 t-Bu H ClOCH₂CF₃ Br CF3 t-Bu H Cl OCH₂CF₃ F CF3 Me Me Cl OCH₂CF₃ Br CF3 Me Me BrOCH₂CF₃ F CF3 Me H Br OCH₂CF₃ Br CF3 Me H Br OCH₂CF₃ F CF3 Et H BrOCH₂CF₃ Br CF3 Et H Br OCH₂CF₃ F CF3 i-Pr H Br OCH₂CF₃ Br CF3 i-Pr H BrOCH₂CF₃ F CF3 t-Bu H Br OCH₂CF₃ Br CF3 t-Bu H Br OCH₂CF₃ F CF3 Me Me BrOCH₂CF₃ Br CF3 Me Me

[0261] TABLE 9

R⁶ R^(5(a)) R^(5(b)) R^(4(a)) R^((b)) R³ V R⁶ R^(5(a)) R^(5(b)) R^(4(a))R^((b)) R³ V Me CF₃ H Me H i-Pr CCl Me CF₃ H Me H CH₂C≡CH CH Cl CF₃ H MeH i-Pr CCl Cl CF₃ H Me H CH₂C≡CH CH F CF₃ H Me H i-Pr CF F CF₃ H Me HCH₂C≡CH CH Me CF₃ H Me H t-Bu CCl Me CF₃ H Me H CH₂C≡CH CCl Cl CF₃ H MeH t-Bu CCl Cl CF₃ H Me H CH₂C≡CH CCl F CF₃ H Me H t-Bu CF F CF₃ H Me HCH₂C≡CH CF Me CF₃ H Me H Me CCl Me CF₃ H Me H CH₂C≡CH N Cl CF₃ H Me H MeCCl Cl CF₃ H Me H CH₂C≡CH N F CF₃ H Me H Me CF F CF₃ H Me H CH₂C≡CH N MeCF₃ H Me H Et CCl Me CO₂Me H Me H i-Pr CH Cl CF₃ H Me H Et CCl Cl CO₂MeH Me H i-Pr CH F CF₃ H Me H Et CF F CO₂Me H Me H i-Pr CH Me Br H Me Hi-Pr CCl Me CO₂Me H Me H i-Pr CCl Cl Br H Me H i-Pr CCl Cl CO₂Me H Me Hi-Pr CCl F Br H Me H i-Pr CF F CO₂Me H Me H i-Pr CF Me CF₃ H Cl H t-BuCCl Me CO₂Me H Me H i-Pr N Cl CF₃ H Cl H t-Bu CCl Cl CO₂Me H Me H i-Pr NF CF₃ H Cl H t-Bu CF F CO₂Me H Me H i-Pr N Me CF₃ H Cl H i-Pr CCl Me CF₃H Cl H CH₂C≡CH CH Cl CF₃ H CI H i-Pr CCl Cl CF₃ H Cl H CH₂C≡CH CH F CF₃H CI H i-Pr CF F CF₃ H Cl H CH₂C≡CH CH Me CF₃ H Me Br i-Pr CCl Me CF₃ HCl H CH₂C≡CH CCl Cl CF₃ H Me Br i-Pr CCl Cl CF₃ H Cl H CH₂C≡CH CCl F CF₃H Me Br i-Pr CF F CF₃ H Cl H CH₂C≡CH CF Me CF₃ Me Me H i-Pr CCl Me CF₃ HCl H CH₂C≡CH N Cl CF₃ Me Me H i-Pr CCl Cl CF₃ H Cl H CH₂C≡CH N F CF₃ MeMe H i-Pr CF F CF₃ H Cl H CH₂C≡CH N Me CF₃ Me Me H i-Pr CH Me CF₃ Me MeH i-Pr N Cl CF₃ Me Me H i-Pr CH Cl CF₃ Me Me H i-Pr N F CF₃ Me Me H i-PrCH F CF₃ Me Me H i-Pr N

[0262] TABLE 10

R⁶ R^(5(a)) R^(5(b)) R^(4(a)) R^((b)) R³ V R⁶ R^(5(a)) R^(5(b)) R^(4(a))R^((b)) R³ V Me CF₃ H Me H i-Pr CH Me CF₃ H Me H CH₂C≡CH CH Cl CF₃ H MeH i-Pr CH Cl CF₃ H Me H CH₂C≡CH CH F CF₃ H Me H i-Pr CH F CF₃ H Me HCH₂C≡CH CH Me CF₃ H Me H i-Pr CCl Me CF₃ H Me H CH₂C≡CH CCl Cl CF₃ H MeH i-Pr CCl Cl CF₃ H Me H CH₂C≡CH CCl F CF₃ H Me H i-Pr CF F CF₃ H Me HCH₂C≡CH CF Me CF₃ H Me H i-Pr N Me CF₃ H Me H CH₂C≡CH N Cl CF₃ H Me Hi-Pr N Cl CF₃ H Me H CH₂C≡CH N F CF₃ H Me H i-Pr N F CF₃ H Me H CH₂C≡CHN Me CF₃ H Me H t-Bu CH Me CF₃ H Me Br i-Pr CH Cl CF₃ H Me H t-Bu CH ClCF₃ H Me Br i-Pr CH F CF₃ H Me H t-Bu CH F CF₃ H Me Br i-Pr CH Me CF₃ HMe H t-Bu CCl Me CF₃ H Me Br i-Pr CCl Cl CF₃ H Me H t-Bu CCl Cl CF₃ H MeBr i-Pr CCl F CF₃ H Me H t-Bu CF F CF₃ H Me Br i-Pr CF Me CF₃ H Me Ht-Bu N Me CF₃ H Me Br i-Pr N Cl CF₃ H Me H t-Bu N Cl CF₃ H Me Br i-Pr NF CF₃ H Me H t-Bu N F CF₃ H Me Br i-Pr N Me CF₃ H Me H Me CH Me CF₃ MeMe H i-Pr CH Cl CF₃ H Me H Me CH Cl CF₃ Me Me H i-Pr CH F CF₃ H Me H MeCH F CF₃ Me Me H i-Pr CH Me CF₃ H Me H Me CCl Me CF₃ Me Me H i-Pr CCl ClCF₃ H Me H Me CCl Cl CF₃ Me Me H i-Pr CCl F CF₃ H Me H Me CF F CF₃ Me MeH i-Pr CF Me CF₃ H Me H Me N Me CF₃ Me Me H i-Pr N Cl CF₃ H Me H Me N ClCF₃ Me Me H i-Pr N F CF₃ H Me H Me N F CF₃ Me Me H i-Pr N Me CF₃ H Me HEt CH Me CO₂Me H Me H i-Pr CH Cl CF₃ H Me H Et CH Cl CO₂Me H Me H i-PrCH F CF₃ H Me H Et CH F CO₂Me H Me H i-Pr CH Me CF₃ H Me H Et CCl MeCO₂Me H Me H i-Pr CCl Cl CF₃ H Me H Et CCl Cl CO₂Me H Me H i-Pr CCl FCF₃ H Me H Et CF F CO₂Me H Me H i-Pr CF Me CF₃ H Me H Et N Me CO₂Me H MeH i-Pr N Cl CF₃ H Me H Et N Cl CO₂Me H Me H i-Pr N F CF₃ H Me H Et N FCO₂Me H Me H i-Pr N Me Br H Me H i-Pr CH Me CF₃ H Cl H i-Pr CH Cl Br HMe H i-Pr CH Cl CF₃ H Cl H i-Pr CH F Br H Me H i-Pr CH F CF₃ H Cl H i-PrCH Me Br H Me H i-Pr CCl Me CF₃ H Cl H i-Pr CCl Cl Br H Me H i-Pr CCl ClCF₃ H Cl H i-Pr CCl F Br H Me H i-Pr CF F CF₃ H Cl H i-Pr CF Me Br H MeH i-Pr N Me CF₃ H Cl H i-Pr N Cl Br H Me H i-Pr N Cl CF₃ H Cl H i-Pr N FBr H Me H i-Pr N F CF₃ H Cl H i-Pr N Me CF₃ H Cl H t-Bu CH Me CF₃ H Cl HCH₂C≡CH CH Cl CF₃ H Cl H t-Bu CH Cl CF₃ H Cl H CH₂C≡CH CH F CF₃ H Cl Ht-Bu CH F CF₃ H Cl H CH₂C≡CH CH Me CF₃ H Cl H t-Bu CCl Me CF₃ H Cl HCH₂C≡CH CCl Cl CF₃ H Cl H t-Bu CCl Cl CF₃ H Cl H CH₂C≡CH CCl F CF₃ H ClH t-Bu CF F CF₃ H Cl H CH₂C≡CH CF Me CF₃ H Cl H t-Bu N Me CF₃ H Cl HCH₂C≡CH N Cl CF₃ H Cl H t-Bu N Cl CF₃ H Cl H CH₂C≡CH N F CF₃ H Cl H t-BuN F CF₃ H Cl H CH₂C≡CH N

[0263] TABLE 11

R⁶ R^(5(a)) R^(5(b)) R^(4(a)) R^((b)) R³ V R⁶ R^(5(a)) R^(5(b)) R^(4(a))R^((b)) R³ V Me CF₃ H Me H i-Pr CH Me CF₃ H Me H CH₂≡CH CH Cl CF₃ H Me Hi-Pr CH Cl CF₃ H Me H CH₂≡CH CH F CF₃ H Me H i-Pr CH F CF₃ H Me H CH₂≡CHCH Me CF₃ H Me H i-Pr CCl Me CF₃ H Me H CH₂≡CH CCl Cl CF₃ H Me H i-PrCCl Cl CF₃ H Me H CH₂≡CH CCl F CF₃ H Me H i-Pr CF F CF₃ H Me H CH₂≡CH CFMe CF₃ H Me H i-Pr N Me CF₃ H Me H CH₂≡CH N Cl CF₃ H Me H i-Pr N Cl CF₃H Me H CH₂≡CH N F CF₃ H Me H i-Pr N F CF₃ H Me H CH₂≡CH N Me CF₃ H Me Ht-Bu CH Me CF₃ H Me Br i-Pr CH Cl CF₃ H Me H t-Bu CH Cl CF₃ H Me Br i-PrCH F CF₃ H Me H t-Bu CH F CF₃ H Me Br i-Pr CH Me CF₃ H Me H t-Bu CCl MeCF₃ H Me Br i-Pr CCl Cl CF₃ H Me H t-Bu CCl Cl CF₃ H Me Br i-Pr CCl FCF₃ H Me H t-Bu CF F CF₃ H Me Br i-Pr CF Me CF₃ H Me H t-Bu N Me CF₃ HMe Br i-Pr N Cl CF₃ H Me H t-Bu N Cl CF₃ H Me Br i-Pr N F CF₃ H Me Ht-Bu N F CF₃ H Me Br i-Pr N Me CF₃ H Me H Me CH Me CF₃ Me Me H i-Pr CHCl CF₃ H Me H Me CH Cl CF₃ Me Me H i-Pr CH F CF₃ H Me H Me CH F CF₃ MeMe H i-Pr CH Me CF₃ H Me H Me CCl Me CF₃ Me Me H i-Pr CCl Cl CF₃ H Me HMe CCl Cl CF₃ Me Me H i-Pr CCl F CF₃ H Me H Me CF F CF₃ Me Me H i-Pr CFMe CF₃ H Me H Me N Me CF₃ Me Me H i-Pr N Cl CF₃ H Me H Me N Cl CF₃ Me MeH i-Pr N F CF₃ H Me H Me N F CF₃ Me Me H i-Pr N Me CF₃ H Me H Et CH MeCO₂Me H Me H i-Pr CH Cl CF₃ H Me H Et CH Cl CO₂Me H Me H i-Pr CH F CF₃ HMe H Et CH F CO₂Me H Me H i-Pr CH Me CF₃ H Me H Et CCl Me CO₂Me H Me Hi-Pr CCl Cl CF₃ H Me H Et CCl Cl CO₂Me H Me H i-Pr CCl F CF₃ H Me H EtCF F CO₂Me H Me H i-Pr CF Me CF₃ H Me H Et N Me CO₂Me H Me H i-Pr N ClCF₃ H Me H Et N Cl CO₂Me H Me H i-Pr N F CF₃ H Me H Et N F CO₂Me H Me Hi-Pr N Me Br H Me H i-Pr CH Me CF₃ H Cl H i-Pr CH Cl Br H Me H i-Pr CHCl CF₃ H Cl H i-Pr CH F Br H Me H i-Pr CH F CF₃ H Cl H i-Pr CH Me Br HMe H i-Pr CCl Me CF₃ H Cl H i-Pr CCl Cl Br H Me H i-Pr CCl Cl CF₃ H Cl Hi-Pr CCl F Br H Me H i-Pr CF F CF₃ H Cl H i-Pr CF Me Br H Me H i-Pr N MeCF₃ H Cl H i-Pr N Cl Br H Me H i-Pr N Cl CF₃ H Cl H i-Pr N F Br H Me Hi-Pr N F CF₃ H Cl H i-Pr N Me CF₃ H Cl H t-Bu CH Me CF₃ H Cl H CH₂≡CH CHCl CF₃ H Cl H t-Bu CH Cl CF₃ H Cl H CH₂≡CH CH F CF₃ H Cl H t-Bu CH F CF₃H Cl H CH₂≡CH CH Me CF₃ H Cl H t-Bu CCl Me CF₃ H Cl H CH₂≡CH CCl Cl CF₃H Cl H t-Bu CCl Cl CF₃ H Cl H CH₂≡CH CCl F CF₃ H Cl H t-Bu CF F CF₃ H ClH CH₂≡CH CF Me CF₃ H Cl H t-Bu N Me CF₃ H Cl H CH₂≡CH N Cl CF₃ H Cl Ht-Bu N Cl CF₃ H Cl H CH₂≡CH N F CF₃ H Cl H t-Bu N F CF₃ H Cl H CH₂≡CH N

[0264] TABLE 12

R⁶ R^(5(a)) R^(5(b)) R^(4(a)) R^((b)) R³ V R⁶ R^(5(a)) R^(5(b)) R^(4(a))R^((b)) R³ V Me CF₃ H Me H i-Pr CH Me CF₃ H Me H CH₂C≡CH CH Cl CF₃ H MeH i-Pr CH Cl CF₃ H Me H CH₂C≡CH CH F CF₃ H Me H i-Pr CH F CF₃ H Me HCH₂C≡CH CH Me CF₃ H Me H i-Pr CCl Me CF₃ H Me H CH₂C≡CH CCl Cl CF₃ H MeH i-Pr CCl Cl CF₃ H Me H CH₂C≡CH CCl F CF₃ H Me H i-Pr CF F CF₃ H Me HCH₂C≡CH CF Me CF₃ H Me H i-Pr N Me CF₃ H Me H CH₂C≡CH N Cl CF₃ H Me Hi-Pr N Cl CF₃ H Me H CH₂C≡CH N F CF₃ H Me H i-Pr N F CF₃ H Me H CH₂C≡CHN Me CF₃ H Me H t-Bu CH Me CF₃ H Me Br i-Pr CH Cl CF₃ H Me H t-Bu CH ClCF₃ H Me Br i-Pr CH F CF₃ H Me H t-Bu CH F CF₃ H Me Br i-Pr CH Me CF₃ HMe H t-Bu CCl Me CF₃ H Me Br i-Pr CCl Cl CF₃ H Me H t-Bu CCl Cl CF₃ H MeBr i-Pr CCl F CF₃ H Me H t-Bu CF F CF₃ H Me Br i-Pr CF Me CF₃ H Me Ht-Bu N Me CF₃ H Me Br i-Pr N Cl CF₃ H Me H t-Bu N Cl CF₃ H Me Br i-Pr NF CF₃ H Me H t-Bu N F CF₃ H Me Br i-Pr N Me CF₃ H Me H Me CH Me CF₃ MeMe H i-Pr CH Cl CF₃ H Me H Me CH Cl CF₃ Me Me H i-Pr CH F CF₃ H Me H MeCH F CF₃ Me Me H i-Pr CH Me CF₃ H Me H Me CCl Me CF₃ Me Me H i-Pr CCl ClCF₃ H Me H Me CCl Cl CF₃ Me Me H i-Pr CCl F CF₃ H Me H Me CF F CF₃ Me MeH i-Pr CF Me CF₃ H Me H Me N Me CF₃ Me Me H i-Pr N Cl CF₃ H Me H Me N ClCF₃ Me Me H i-Pr N F CF₃ H Me H Me N F CF₃ Me Me H i-Pr N Me CF₃ H Me HEt CH Me CO₂Me H Me H i-Pr CH Cl CF₃ H Me H Et CH Cl CO₂Me H Me H i-PrCH F CF₃ H Me H Et CH F CO₂Me H Me H i-Pr CH Me CF₃ H Me H Et CCl MeCO₂Me H Me H i-Pr CCl Cl CF₃ H Me H Et CCl Cl CO₂Me H Me H i-Pr CCl FCF₃ H Me H Et CF F CO₂Me H Me H i-Pr CF Me CF₃ H Me H Et N Me CO₂Me H MeH i-Pr N Cl CF₃ H Me H Et N Cl CO₂Me H Me H i-Pr N F CF₃ H Me H Et N FCO₂Me H Me H i-Pr N Me Br H Me H i-Pr CH Me CF₃ H Cl H i-Pr CH Cl Br HMe H i-Pr CH Cl CF₃ H Cl H i-Pr CH F Br H Me H i-Pr CH F CF₃ H Cl H i-PrCH Me Br H Me H i-Pr CCl Me CF₃ H Cl H i-Pr CCl Cl Br H Me H i-Pr CCl ClCF₃ H Cl H i-Pr CCl F Br H Me H i-Pr CF F CF₃ H Cl H i-Pr CF Me Br H MeH i-Pr N Me CF₃ H Cl H i-Pr N Cl Br H Me H i-Pr N Cl CF₃ H Cl H i-Pr N FBr H Me H i-Pr N F CF₃ H Cl H i-Pr N Me CF₃ H Cl H t-Bu CH Me CF₃ H Cl HCH₂C≡CH CH Cl CF₃ H Cl H t-Bu CH Cl CF₃ H Cl H CH₂C≡CH CH F CF₃ H Cl Ht-Bu CH F CF₃ H Cl H CH₂C≡CH CH Me CF₃ H Cl H t-Bu CCl Me CF₃ H Cl HCH₂C≡CH CCl Cl CF₃ H Cl H t-Bu CCl Cl CF₃ H Cl H CH₂C≡CH CCl F CF₃ H ClH t-Bu CF F CF₃ H Cl H CH₂C≡CH CF Me CF₃ H Cl H t-Bu N Me CF₃ H Cl HCH₂C≡CH N Cl CF₃ H Cl H t-Bu N Cl CF₃ H Cl H CH₂C≡CH N F CF₃ H Cl H t-BuN F CF₃ H Cl H CH₂C≡CH N

[0265] TABLE 13

R⁶ R^(5(a)) R^(5(b)) R^(4(a)) R^((b)) R³ V R⁶ R^(5(a)) R^(5(b)) R^(4(a))R^((b)) R³ V X is O Me CF₃ H Me H i-Pr CH Me CF₃ H Me H CH₂C≡CH CH ClCF₃ H Me H i-Pr CH Cl CF₃ H Me H CH₂C≡CH CH F CF₃ H Me H i-Pr CH F CF₃ HMe H CH₂C≡CH CH Me CF₃ H Me H i-Pr CCl Me CF₃ H Me H CH₂C≡CH CCl Cl CF₃H Me H i-Pr CCl Cl CF₃ H Me H CH₂C≡CH CCl F CF₃ H Me H i-Pr CF F CF₃ HMe H CH₂C≡CH CF Me CF₃ H Me H i-Pr N Me CF₃ H Me H CH₂C≡CH N Cl CF₃ H MeH i-Pr N Cl CF₃ H Me H CH₂C≡CH N F CF₃ H Me H i-Pr N F CF₃ H Me HCH₂C≡CH N Me CF₃ H Me H t-Bu CH Me CF₃ H Me Br i-Pr CH Cl CF₃ H Me Ht-Bu CH Cl CF₃ H Me Br i-Pr CH F CF₃ H Me H t-Bu CH F CF₃ H Me Br i-PrCH Me CF₃ H Me H t-Bu CCl Me CF₃ H Me Br i-Pr CCl Cl CF₃ H Me H t-Bu CClCl CF₃ H Me Br i-Pr CCI F CF₃ H Me H t-Bu CF F CF₃ H Me Br i-Pr CF MeCF₃ H Me H t-Bu N Me CF₃ H Me Br i-Pr N Cl CF₃ H Me H t-Bu N Cl CF₃ H MeBr i-Pr N F CF₃ H Me H t-Bu N F CF₃ H Me Br i-Pr N Me CF₃ H Me H Me CHMe CF₃ Me Me H i-Pr CH Cl CF₃ H Me H Me CH Cl CF₃ Me Me H i-Pr CH F CF₃H Me H Me CH F CF₃ Me Me H i-Pr CH Me CF₃ H Me H Me CCl Me CF₃ Me Me Hi-Pr CCl Cl CF₃ H Me H Me CCl Cl CF₃ Me Me H i-Pr CCl F CF₃ H Me H Me CFF CF₃ Me Me H i-Pr CF Me CF₃ H Me H Me N Me CF₃ Me Me H i-Pr N Cl CF₃ HMe H Me N Cl CF₃ Me Me H i-Pr N F CF₃ H Me H Me N F CF₃ Me Me H i-Pr NMe CF₃ H Me H Et CH Me CO₂Me H Me H i-Pr CH Cl CF₃ H Me H Et CH Cl CO₂MeH Me H i-Pr CH F CF₃ H Me H Et CH F CO₂Me H Me H i-Pr CH Me CF₃ H Me HEt CCl Me CO₂Me H Me H i-Pr CCl Cl CF₃ H Me H Et CCl Cl CO₂Me H Me Hi-Pr CCl F CF₃ H Me H Et CF F CO₂Me H Me H i-Pr CF Me CF₃ H Me H Et N MeCO₂Me H Me H i-Pr N Cl CF₃ H Me H Et N Cl CO₂Me H Me H i-Pr N F CF₃ H MeH Et N F CO₂Me H Me H i-Pr N Me Br H Me H i-Pr CH Me CF₃ H Cl H i-Pr CHCl Br H Me H i-Pr CH Cl CF₃ H Cl H i-Pr CH F Br H Me H i-Pr CH F CF₃ HCl H i-Pr CH Me Br H Me H i-Pr CCl Me CF₃ H Cl H i-Pr CCl Cl Br H Me Hi-Pr CCl Cl CF₃ H Cl H i-Pr CCl F Br H Me H i-Pr CF F CF₃ H Cl H i-Pr CFMe Br H Me H i-Pr N Me CF₃ H Cl H i-Pr N Cl Br H Me H i-Pr N Cl CF₃ H ClH i-Pr N F Br H Me H i-Pr N F CF₃ H Cl H i-Pr N Me CF₃ H Cl H t-Bu CH MeCF₃ H Cl H CH₂C≡CH CH Cl CF₃ H Cl H t-Bu CH Cl CF₃ H Cl H CH₂C≡CH CH FCF₃ H Cl H t-Bu CH F CF₃ H Cl H CH₂C≡CH CH Me CF₃ H Cl H t-Bu CCl Me CF₃H Cl H CH₂C≡CH CCl Cl CF₃ H Cl H t-Bu CCl Cl CF₃ H Cl H CH₂C≡CH CCl FCF₃ H Cl H t-Bu CF F CF₃ H Cl H CH₂C≡CH CF Me CF₃ H Cl H t-Bu N Me CF₃ HCl H CH₂C≡CH N Cl CF₃ H Cl H t-Bu N Cl CF₃ H Cl H CH₂C≡CH N F CF₃ H Cl Ht-Bu N F CF₃ H Cl H CH₂C≡CH N X is S Me CF₃ H Me H i-Pr CH Me CF₃ H Me HCH₂C≡CH CH Cl CF₃ H Me H i-Pr CH Cl CF₃ H Me H CH₂C≡CH CH F CF₃ H Me Hi-Pr CH F CF₃ H Me H CH₂C≡CH CH Me CF₃ H Me H i-Pr CCl Me CF₃ H Me HCH₂C≡CH CCl Cl CF₃ H Me H i-Pr CCl Cl CF₃ H Me H CH₂C≡CH CCl F CF₃ H MeH i-Pr CF F CF₃ H Me H CH₂C≡CH CF Me CF₃ H Me H i-Pr N Me CF₃ H Me HCH₂C≡CH N Cl CF₃ H Me H i-Pr N Cl CF₃ H Me H CH₂C≡CH N F CF₃ H Me H i-PrN F CF₃ H Me H CH₂C≡CH N Me CF₃ H Me H t-Bu CH Me CF₃ H Me Br i-Pr CH ClCF₃ H Me H t-Bu CH Cl CF₃ H Me Br i-Pr CH F CF₃ H Me H t-Bu CH F CF₃ HMe Br i-Pr CH Me CF₃ H Me H t-Bu CCl Me CF₃ H Me Br i-Pr CCl Cl CF₃ H MeH t-Bu CCl Cl CF₃ H Me Br i-Pr CCl F CF₃ H Me H t-Bu CF F CF₃ H Me Bri-Pr CF Me CF₃ H Me H t-Bu N Me CF₃ H Me Br i-Pr N Cl CF₃ H Me H t-Bu NCl CF₃ H Me Br i-Pr N F CF₃ H Me H t-Bu N F CF₃ H Me Br i-Pr N Me CF₃ HMe H Me CH Me CF₃ Me Me H i-Pr CH Cl CF₃ H Me H Me CH Cl CF₃ Me Me Hi-Pr CH F CF₃ H Me H Me CH F CF₃ Me Me H i-Pr CH Me CF₃ H Me H Me CCl MeCF₃ Me Me H i-Pr CCl Cl CF₃ H Me H Me CCl Cl CF₃ Me Me H i-Pr CCl F CF₃H Me H Me CF F CF₃ Me Me H i-Pr CF Me CF₃ H Me H Me N Me CF₃ Me Me Hi-Pr N Cl CF₃ H Me H Me N Cl CF₃ Me Me H i-Pr N F CF₃ H Me H Me N F CF₃Me Me H i-Pr N Me CF₃ H Me H Et CH Me CO₂Me H Me H i-Pr CH Cl CF₃ H Me HEt CH Cl CO₂Me H Me H i-Pr CH F CF₃ H Me H Et CH F CO₂Me H Me H i-Pr CHMe CF₃ H Me H Et CCl Me CO₂Me H Me H i-Pr CCl Cl CF₃ H Me H Et CCl ClCO₂Me H Me H i-Pr CCl F CF₃ H Me H Et CF F CO₂Me H Me H i-Pr CF Me CF₃ HMe H Et N Me CO₂Me H Me H i-Pr N Cl CF₃ H Me H Et N Cl CO₂Me H Me H i-PrN F CF₃ H Me H Et N F CO₂Me H Me H i-Pr N Me Br H Me H i-Pr CH Me CF₃ HCl H i-Pr CH Cl Br H Me H i-Pr CH Cl CF₃ H Cl H i-Pr CH F Br H Me H i-PrCH F CF₃ H Cl H i-Pr CH Me Br H Me H i-Pr CCl Me CF₃ H Cl H i-Pr CCl ClBr H Me H i-Pr CCl Cl CF₃ H Cl H i-Pr CCl F Br H Me H i-Pr CF F CF₃ H ClH i-Pr CF Me Br H Me H i-Pr N Me CF₃ H Cl H i-Pr N Cl Br H Me H i-Pr NCl CF₃ H Cl H i-Pr N F Br H Me H i-Pr N F CF₃ H Cl H i-Pr N Me CF₃ H ClH t-Bu CH Me CF₃ H Cl H CH₂C≡CH CH Cl CF₃ H Cl H t-Bu CH Cl CF₃ H Cl HCH₂C≡CH CH F CF₃ H Cl H t-Bu CH F CF₃ H Cl H CH₂C≡CH CH Me CF₃ H Cl Ht-Bu CCl Me CF₃ H Cl H CH₂C≡CH CCl Cl CF₃ H Cl H t-Bu CCl Cl CF₃ H Cl HCH₂C≡CH CCl F CF₃ H Cl H t-Bu CF F CF₃ H Cl H CH₂C≡CH CF Me CF₃ H Cl Ht-Bu N Me CF₃ H Cl H CH₂C≡CH N Cl CF₃ H Cl H t-Bu N Cl CF₃ H Cl HCH₂C≡CH N F CF₃ H Cl H t-Bu N F CF₃ H Cl H CH₂C≡CH N

[0266] Formulation/Utility

[0267] Compounds of this invention will generally be used as aformulation or composition with an agriculturally suitable carriercomprising at least one of a liquid diluent, a solid diluent or asurfactant. The formulation or composition ingredients are selected tobe consistent with the physical properties of the active ingredient,mode of application and environmental factors such as soil type,moisture and temperature. Useful formulations include liquids such assolutions (including emulsifiable concentrates), suspensions, emulsions(including microemulsions and/or suspoemulsions) and the like whichoptionally can be thickened into gels. Useful formulations furtherinclude solids such as dusts, powders, granules, pellets, tablets,films, and the like which can be water-dispersible (“wettable”) orwater-soluble. Active ingredient can be (micro)encapsulated and furtherformed into a suspension or solid formulation; alternatively the entireformulation of active ingredient can be encapsulated (or “overcoated”).Encapsulation can control or delay release of the active ingredient.Sprayable formulations can be extended in suitable media and used atspray volumes from about one to several hundred liters per hectare.High-strength compositions are primarily used as intermediates forfurther formulation.

[0268] The formulations will typically contain effective amounts ofactive ingredient, diluent and surfactant within the followingapproximate ranges that add up to 100 percent by weight. Weight PercentActive Ingredient Diluent Surfactant Water-Dispersible 5-90 0-94 1-15and Water-soluble Granules, Tablets and Powders. Suspensions, 5-5040-95  0-15 Emulsions, Solutions (including Emulsifiable Concentrates)Dusts 1-25 70-99  0-5  Granules and 0.01-99     5-99.99 0-15 PelletsHigh Strength 90-99  0-10 0-2  Compositions

[0269] Typical solid diluents are described in Watkins, et al., Handbookof Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books,Caldwell, N.J. Typical liquid diluents are described in Marsden,Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 'sDetergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, N.J.,as well as Sisely and Wood, Encyclopedia of Surface Active Agents,Chemical Publ. Co., Inc., New York, 1964, list surfactants andrecommended uses. All formulations can contain minor amounts ofadditives to reduce foam, caking, corrosion, microbiological growth andthe like, or thickeners to increase viscosity.

[0270] Surfactants include, for example, polyethoxylated alcohols,polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acidesters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzenesulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates,naphthalene sulfonate formaldehyde condensates, polycarboxylates, andpolyoxyethylene/polyoxypropylene block copolymers. Solid diluentsinclude, for example, clays such as bentonite, montmorillonite,attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth,urea, calcium carbonate, sodium carbonate and bicarbonate, and sodiumsulfate. Liquid diluents include, for example, water,N,]dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethyleneglycol, polypropylene glycol, paraffins, alkylbenzenes,alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn,peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters,ketones such as cyclohexanone, 2-heptanone, isophorone and4-hydroxy4-methyl-2-pentanone, and alcohols such as methanol,cyclohexanol, decanol and tetrahydrofurfuryl alcohol.

[0271] Solutions, including emulsifiable concentrates, can be preparedby simply mixing the ingredients. Dusts and powders can be prepared byblending and, usually, grinding as in a hammer mill or fluid-energymill. Suspensions are usually prepared by wet-milling; see, for example,U.S. Pat. No. 3,060,084. Granules and pellets can be prepared byspraying the active material upon preformed granular carriers or byagglomeration techniques. See Browning, “Agglomeration”, ChemicalEngineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer'sHandbook, 4th Ed., McGraw-Hill, N.Y., 1963, pages 8-57 and following,and PCT Publication WO 91/13546. Pellets can be prepared as described inU.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granulescan be prepared as taught in U.S. Pat. No. 4,144,050, U.S. Pat. No.3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S.Pat. No. 5,180,587, U.S. Pat. No. 5,232,701 and U.S. Pat. No. 5,208,030.Films can be prepared as taught in GB 2,095,558 and U.S. Pat. No.3,299,566.

[0272] For further information regarding the art of formulation, see T.S. Woods, “The Formulator's Toolbox—Product Forms for Modem Agriculture”in Pesticide Chemistry and Bioscience, The Food—Environment Challenge,T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th InternationalCongress on Pesticide Chemistry, The Royal Society of Chemistry,Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6,line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No.3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12,15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 andExamples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons,Inc., New York, 1961, pp 81-96; and Hance et al., Weed Control Handbook,8th Ed., Blackwell Scientific Publications, Oxford, 1989.

[0273] In the following Examples, all percentages are by weight and allformulations are prepared in conventional ways. Compound numbers referto compounds in Index Table A.

EXAMPLE A

[0274] Wettable Powder Compound 1 65.0%  dodecylphenol polyethyleneglycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate6.0% montmorillonite (calcined)  23.0%. 

EXAMPLE B

[0275] Granule Compound 1 10.0% attapulgite granules (low volatilematter,  90.0%. 0.71/0.30 mm; U.S.S. No. 25-50 sieves)

EXAMPLE C

[0276] Extruded Pellet Compound 1 25.0% anhydrous sodium sulfate 10.0%crude calcium ligninsulfonate  5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite  59.0%.

EXAMPLE D

[0277] Emulsifiable Concentrate Compound 1 20.0% blend of oil solublesulfonates 10.0% and polyoxyethylene ethers isophorone  70.0%.

EXAMPLE E

[0278] Granule Compound 1 0.5% cellulose 2.5% lactose 4.0% cornmeal 93.0%. 

[0279] Compounds of this invention are characterized by favorablemetabolic and/or soil residual patterns and exhibit activity controllinga spectrum of agronomic and non-agronomic invertebrate pests. (In thecontext of this disclosure “invertebrate pest control” means inhibitionof invertebrate pest development (including mortality) that causessignificant reduction in feeding or other injury or damage caused by thepest; related expressions are defined analogously.) As referred to inthis disclosure, the term “invertebrate pest” includes arthropods,gastropods and nematodes of economic importance as pests. The term“arthropod” includes insects, mites, spiders, scorpions, centipedes,millipedes, pill bugs and symphylans. The term “gastropod” includessnails, slugs and other Stylommatophora. The term “nematode” includesall of the helminths, such as: roundworms, heartworms, and phytophagousnematodes (Nematoda), flukes (Tematoda), Acanthocephala, and tapeworms(Cestoda). Those skilled in the art will recognize that not allcompounds are equally effective against all pests. Compounds of thisinvention display activity against economically important agronomic andnonagronomic pests. The term “agronomic” refers to the production offield crops such as for food and fiber and includes the growth of cerealcrops (e.g., wheat, oats, barley, rye, rice, maize), soybeans, vegetablecrops (e.g., lettuce, cabbage, tomatoes, beans), potatoes, sweetpotatoes, grapes, cotton, and tree fruits (e.g., pome fruits, stonefruits and citrus fruits). The term “nonagronomic” refers to otherhorticultural (e.g., forest, greenhouse, nursery or ornamental plantsnot grown in a field), public (human) and animal health, domestic andcommercial structure, household, and stored product applications orpests. For reason of invertebrate pest control spectrum and economicimportance, protection (from damage or injury caused by invertebratepests) of agronomic crops of cotton, maize, soybeans, rice, vegetablecrops, potato, sweet potato, grapes and tree fruit by controllinginvertebrate pests are preferred embodiments of the invention. Agronomicor nonagronomic pests include larvae of the order Lepidoptera, such asarmyworms, cutworms, loopers, and heliothines in the family Noctuidae(e.g., fall armyworm (Spodoptera fugiperda J. E. Smith), beet armyworm(Spodoptera exigua Hübner), black cutworm (Agrotis ipsilon Hufnagel),cabbage looper (Trichoplusia ni Hübner), tobacco budworm (Heliothisvirescens Fabricius)); borers, casebearers, webworms, coneworms,cabbageworms and skeletonizers from the family Pyralidae (e.g., Europeancorn borer (Ostrinia nubilalis Hübner), navel orangeworm (Amyeloistransitella Walker), corn root webworm (Crambus caliginosellus Clemens),sod webworm (Herpetogramma licarsisalis Walker)); leafrollers, budworms,seed worms, and fruit worms in the family Tortricidae (e.g., codlingmoth (Cydia pomonella Linnaeus), grape berry moth (Endopiza viteanaClemens), oriental fruit moth (Grapholita molesta Busck)); and manyother economically important lepidoptera (e.g., diamondback moth(Plutella xylostella Linnaeus), pink bollworm (Pectinophora gossypiellaSaunders), gypsy moth (Lymantria dispar Linnaeus)); nymphs and adults ofthe order Blattodea including cockroaches from the families Blattellidaeand Blattidae (e.g., oriental cockroach (Blatta orientalis Linnaeus),Asian cockroach (Blatella asahinai Mizukubo), German cockroach(Blattella germanica Linnaeus), brownbanded cockroach (Supellalongipalpa Fabricius), American cockroach (Periplaneta americanaLinnaeus), brown cockroach (Periplaneta brunnea Burmeister), Madeiracockroach (Leucophaea maderae Fabricius)); foliar feeding larvae andadults of the order Coleoptera including weevils from the familiesAnthribidae, Bruchidae, and Curculionidae (e.g., boll weevil (Anthonomusgrandis Boheman), rice water weevil (Lissorhoptrus oryzophilus Kuschel),granary weevil (Sitophilus granarius Linnaeus), rice weevil (Sitophilusoryzae Linnaeus)); flea beetles, cucumber beetles, rootworms, leafbeetles, potato beetles, and leafminers in the family Chrysomelidae(e.g., Colorado potato beetle (Leptinotarsa decemlineata Say), westerncorn rootworm (Diabrotica virgifera virgifera LeConte)); chafers andother beetles from the family Scaribaeidae (e.g., Japanese beetle(Popillia japonica Newman) and European chafer (Rhizotrogus majalisRazoumowsky)); carpet beetles froim the family Dermestidae; wirewormsfrom the family Elateridae; bark beetles from the family Scolytidae andflour beetles from the family Tenebrionidae. In addition agronoomic andnonagronomic pests include: adults and larvae of the order Dermapteraincluding earwigs from the family Forficulidae (e.g., European earwig(Forficula auricularia Linnaeus), black earwig (Chelisoches morioFabricius)); adults and nymphs of the orders Hemiptera and Homopterasuch as, plant bugs from the family Miridae, cicadas from the familyCicadidae, leafhoppers (e.g. Empoasca spp.) from the familyCicadellidae, planthoppers from the families Fulgoroidae andDelphacidae, treehoppers from the family Membracidae, psyllids from thefamily Psyllidae, whiteflies from the family Aleyrodidae, aphids fromthe family Aphididae, phylloxera from the family Phylloxeridae,mealybugs from the family Pseudococcidae, scales from the familiesCoccidae, Diaspididae and Margarodidae, lace bugs from the familyTingidae, stink bugs from the family Pentatomidae, cinch bugs (e.g.,Blissus spp.) and other seed bugs from the family Lygaeidae, spittlebugsfrom the family Cercopidae squash bugs from the family Coreidae, and redbugs and cotton stainers from the family Pyrrhocoridae. Also includedare adults and larvae of the order Acari (mites) such as spider mitesand red mites in the family Tetranychidae (e.g., European red mite(Panonychus ulmi Koch), two spotted spider mite (Tetranychus urticaeKoch), McDaniel mite (Tetranychus mcdanieli McGregor)), flat mites inthe family Tenuipalpidae (e.g., citrus flat mite (Brevipalpus lewisiMcGregor)), rust and bud mitesin the family Eriophyidae and other foliarfeeding mites and mites important in human and animal health, i.e. dustmites in the family Epidermoptidae, follicle mites in the familyDemodicidae, grain mites in the family Glycyphagidae, ticks in the orderIxodidae (e.g., deer tick (Ixodes scapularis Say), Australian paralysistick (Ixodes holocyclus Neumann), American dog tick (Dermacentorvariabilis Say), lone star tick (Amblyomma americanum Linnaeus) and scaband itch mites in the families Psoroptidae, Pyemotidae, and Sarcoptidae;adults and immatures of the order Orthoptera including grasshoppers,locusts and crickets (e.g., migratory grasshoppers (e.g., Melanoplussanguinipes Fabricius, M. differentialis Thomas), American grasshoppers(e.g., Schistocerca americana Drury), desert locust (Schistocercagregaria Forskal), migratory locust (Locusta migratoria Linnaeus), housecricket (Acheta domesticus Linnaeus), mole crickets (Gryllotalpa spp.));adults and immatures of the order Diptera including leafininers, midges,fuit flies (Tephritidae), frit flies (e.g., Oscinella frit Linnaeus),soil maggots, house flies (e.g., Musca domestica Linnaeus), lesser houseflies (e.g., Fannia canicularis Linnaeus, F. femoralis Stein), stableflies (e.g., Stomoxys calcitrans Linnaeus), face flies, horn flies, blowflies (e.g., Chrysomya spp., Phormia spp.), and other muscoid fly pests,horse flies (e.g., Tabanus spp.), bot flies (e.g., Gastrophilus spp.,Oestrus spp.), cattle grubs (e.g., Hypoderma spp.), deer flies (e.g.,Chrysops spp.), keds (e.g., Melophagus ovinus Linnaeus) and otherBrachycera, mosquitoes (e.g., Aedes spp., Anopheles spp., Culex spp.),black flies (e.g., Prosimulium spp., Simulium spp.), biting midges, sandflies, sciarids, and other Nematocera; adults and immatures of the orderThysanoptera including onion thrips (Thrips tabaci Lindeman) and otherfoliar feeding thrips; insect pests of the order Hymenoptera includingants (e.g., red carpenter ant (Camponotus ferrugineus Fabricius), blackcarpenter ant (Camponotus pennsylvanicus De Geer), Pharaoh ant(Monomorium pharaonis Linnaeus), little fire ant (Wasmannia auropunctataRoger), fire ant (Solenopsis geminata Fabricius), red imported fire ant(Solenopsis invicta Buren), Argentine ant (Iridomyrmex humilis Mayr),crazy ant (Paratrechina longicornis Latreille), pavement ant(Tetramorium caespitum Linnaeus), cornfield ant (Lasius alienusFörster), odorous house ant (Tapinoma sessile Say)), bees (includingcarpenter bees), hornets, yellow jackets and wasps; insect pests of theorder Isoptera including the eastern subterranean termite(Reticulitermes flavipes Kollar), western subterranean termite(Reticulitermes hesperus Banks), Formosan subterranean termite(Coptotermes formosanus Shiraki), West Indian drywood termite(Incisitermes immigrans Snyder) and other termites of economicimportance; insect pests of the order Thysanura such as silverfish(Lepisma saccharina Linnaeus) and firebrat (Thermobia domesticaPackard); insect pests of the order Mallophaga and including the headlouse (Pediculus humanus capitis De Geer), body louse (Pediculus humanushumanus Linnaeus), chicken body louse (Menacanthus stramineus Nitszch),dog biting louse (Trichodectes canis De Geer), fluff louse (Goniocotesgallinae De Geer), sheep body louse (Bovicola ovis Schrank), short-nosedcattle louse (Haematopinus eurysternus Nitzsch), long-nosed cattle louse(Linognathus vituli Linnaeus) and other sucking and chewing parasiticlice that attack man and animals; insect pests of the order Siphonopteraincluding the oriental rat flea (Xenopsylla cheopis Rothschild), catflea (Ctenocephalides felis Bouche), dog flea (Ctenocephalides canisCurtis), hen flea (Ceratophyllus gallinae Schrank), sticktight flea(Echidnophaga gallinacea Westwood), human flea (Pulex irritans Linnaeus)and other fleas afflicting mammals and birds. Additional arthropod pestscovered include: spiders in the order Araneae such as the brown reclusespider (Loxosceles reclusa Gertsch & Mulaik) and the black widow spider(Latrodectus mactans Fabricius), and centipedes in the orderScutigeromorpha such as the house centipede (Scutigera coleoptrataLinnaeus). Compounds of the present invention also have activity onmembers of the Classes Nematoda, Cestoda, Trematoda, and Acanthocephalaincluding economically important members of the orders Strongylida,Ascaridida, Oxyurida, Rhabditida, Spirurida, and Enoplida such as butnot limited to economically important agricultural pests (i.e. root knotnematodes in the genus Meloidogyne, lesion nematodes in the genusPratylenchus, stubby root nematodes in the genus Trichodorus, etc.) andanimal and human health pests (i.e. all economically important flukes,tapeworms, and roundworms, such as Strongylus vulgaris in horses,Toxocara canis in dogs, Haemonchus contortus in sheep, Dirofilariaimmitis Leidy in dogs, Anoplocephala perfoliata in horses, Fasciolahepatica Linnaeus in ruminants, etc.).

[0280] Compounds of the invention show particularly high activityagainst pests in the order Lepidoptera (e.g., Alabama argillacea Hübner(cotton leaf worm), Archips argyrospila Walker (fruit tree leaf roller),A. rosana Linnaeus (European leaf roller) and other Archips species,Chilo suppressalis Walker (rice stem borer), Cnaphalocrosis medinalisGuenee (rice leaf roller), Cambus caliginosellus Clemens (corn rootwebworm), Crambus teterrellus Zincken (bluegrass webworm), Cydiapomonella Linnaeus (codling moth), Earias insulana Boisduval (spinybollworm), Earias vittella Fabricius (spotted bollworm), Helicoverpaarmigera Hübner (American bollworm), Helicoverpa zea Boddie (cornearworm), Heliothis virescens Fabricius (tobacco budworm), Herpetogrammalicarsisalis Walker (sod webworm), Lobesia botrana Denis &Schiffermfiller (grape berry moth), Pectinophora gossypiella Saunders(ink bollworm), Phyllocnistis citrella Stainton (citrus leafminer),Pieris brassicae Linnaeus (large white butterfly), Pieris rapae Linnaeus(small white butterfly), Plutella xylostella Linnaeus (diamondbackmoth), Spodoptera exigua Hübner (beet armyworm), Spodoptera lituraFabricius (tobacco cutworm, cluster caterpillar), Spodoptera frugiperdaJ. E. Smith (fall armyworm), Trichoplusia ni Hübner (cabbage looper) andTuta absoluta Meyrick (tomato leafininer)). Compounds of the inventionalso have commercially significant activity on members from the orderHomoptera including: Acyrthisiphon pisum Harris (pea aphid), Aphiscraccivora Koch (cowpea aphid), Aphis fabae Scopoli (black bean aphid),Aphis gossypii Glover (cotton aphid, melon aphid), Aphis pomi De Geer(apple aphid), Aphis spiraecola Patch (spirea aphid), Aulacorthum solaniKaltenbach (foxglove aphid), Chaetosiphon fragaefolii Cockerell(strawberry aphid), Diuraphis noxia Kurdjumov/Mordvilko (Russian wheataphid), Dysaphis plantaginea Paaserini (rosy apple aphid), Eriosomalanigerum Hausmanm (woolly apple aphid), Hyalopterus pruni Geoffroy(mealy plum aphid), Lipaphis erysimi Kaltenbach (turnip aphid),Metopolophium dirrhodum Walker (cereal aphid), Macrosipurn euphorbiaeThomas (potato aphid), Myzus persicae Sulzer (each-potato aphid, greenpeach aphid), Nasonovia ribisnigri Mosley (lettuce aphid), Pemphigusspp. (root aphids and gall aphids), Rhopalosiphum maidis Fitch (cornleaf aphid), Rhopalosiphum padi Linnaeus (bird cherry-oat aphid),Schizaphis graminum Rondani (greenbug), Sitobion avenae Fabricius(English grain aphid), Therioaphis maculata Buckton (spotted alfalfaaphid), Toxoptera aurantii Boyer de Fonscolombe (black citrus aphid),and Toxoptera citricida Kirkaldy (brown citrus aphid); Adelges spp.(adelgids); Phylloxera devastatrix Pergande (pecan phylloxera); Bemisiatabaci Gennadius (tobacco whitefly, sweetpotato whitefly), Bemisiaargentifolii Bellows & Perring (silverleaf whitefly), Dialeurodes citriAshmead (citrus whitefly) and Trialeurodes vaporariorum Westwood(greenhouse whitefly); Empoasca fabae Harris (potato leafhopper),Laodelphax striatellus Fallen (smaller brown planthopper), Macrolestesquadrilineatus Forbes (aster leafhopper), Nephotettix cinticeps Uhler(green leafhopper), Nephotettix nigropictus St{dot over (a)}l (riceleafhopper), Nilaparvata lugens St{dot over (a)}l (brown planthopper),Peregrinus maidis Ashmead (corn planthopper), Sogatella furciferaHorvath (white-backed planthopper), Sogatodes orizicola Muir (ricedelphacid), Tphlocyba pomaria McAtee white apple leafhopper,Erythroneoura spp. (grape leafioppers); Magicidada septendecim Linnaeus(periodical cicada); Icerya purchasi Maskell (cottony cushion scale),Quadraspidiotus perniciosus Comstock (San Jose scale); Planococcus citriRisso (citrus mealybug); Pseudococcus spp. (other mealybug complex);Cacopsylla pyricola Foerster (pear psylla), Trioza diospyri Ashmead(persimmon psylla). These compounds also have activity on members fromthe order Hemiptera including: Acrosternum hilare Say (green stink bug),Anasa tristis De Geer (squash bug), Blissus leucopterus leucopterus Say(chinch bug), Corythuca gossypii Fabricius (cotton lace bug),Cyrtopeltis modesta Distant (tomato bug), Dysdercus suturellusHerrich-Schäffer (cotton stainer), Euchistus servus Say (brown stinkbug), Euchistus variolarius Palisot de Beauvois (one-spotted stink bug),Graptosthetus spp. (complex of seed bugs), Leptoglossus corculus Say(leaf-footed pine seed bug), Lygus lineolaris Palisot de Beauvois(tarnished plant bug), Nezara viridula Linnaeus (southern green stinkbug), Oebalus pugnax Fabricius (rice stink bug), Oncopeltus fasciatusDallas (large milkweed bug), Pseudatomoscelis seriatus Reuter (cottonfleahopper). Other insect orders controlled by compounds of theinvention include Thysanoptera (e.g., Frankliniella occidentalisPergande (western flower thrip), Scirthothrips citri Moulton (citrusthrip), Sericothrips variabilis Beach (soybean thrip), and Thrips tabaciLindeman (onion thrip); and the order Coleoptera (e.g., Leptinotarsadecemlineata Say (Colorado potato beetle), Epilachna varivestis Mulsant(Mexican bean beetle) and wireworms of the genera Agriotes, Athous orLimonius).

[0281] Compounds of this invention can also be mixed with one or moreother biologically active compounds or agents including insecticides,fungicides, nematocides, bactericides, acaricides, growth regulatorssuch as rooting stimulants, chemosterilants, semiochemicals, repellents,attractants, pheromones, feeding stimulants, other biologically activecompounds or entomopathogenic bacteria, virus or fungi to form amulti-component pesticide giving an even broader spectrum ofagricultural utility. Thus compositions of the present invention canfurther comprise a biologically effective amount of at least oneadditional biologically active compound or agent. Examples of suchbiologically active compounds or agents with which compounds of thisinvention can be formulated are: insecticides such as abamectin,acephate, acetamiprid, avermectin, azadirachtin, azinphos-methyl,bifenthrin, binfenazate, buprofezin, carbofuran, chlorfenapyr,chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide,clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin,lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin,diafenthiuron, diazinon, diflubenzuron, dimethoate, diofenolan,emamectin, endosulfan, esfenvalerate, ethiprole, fenothicarb,fenoxycarb, fenpropathrin, fenproximate, fenvalerate, fipronil,flonicamid, flucythrinate, tau-fluvalinate, flufenoxuron, fonophos,halofenozide, hexaflumuron, imidacloprid, indoxacarb, isofenphos,lufenuron, malathion, metaldehyde, methamidophos, methidathion,methomyl, methoprene, methoxychlor, monocrotophos, methoxyfenozide,nithiazin, novaluron, oxamyl, parathion, parathion-methyl, permetrm,phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos,pymetrozine, pyridalyl, pyriproxyfen, rotenone, spinosad, sulprofos,tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos,thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin,trichlorfon and triflumuron; fungicides such as acibenzolar,azoxystrobin, benomyl, blasticidin-S, Bordeaux mixture (tribasic coppersulfate), bromuconazole, carpropamid, captafol, captan, carbendazim,chloroneb, chlorothalonil, copper oxychloride, copper salts,cyflufenamid, cymoxanil, cyproconazole, cyprodinil,(S)-3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide(RH 7281), diclocymet (S-2900), diclomezine, dicloran, difenoconazole,(S)-3,5-dihydro-5-methyl-2-(methylthio)-5-phenyl-3-(phenylamino)-4H-imidazol-4-one(RP 407213), dimethomorph, dimoxystrobin, diniconazole, diniconazole-M,dodine, edifenphos, epoxiconazole, famoxadone, fenamidone, fenarimol,fenbuconazole, fencaramid (SZX0722), fenpiclonil, fenpropidin,fenpropimorph, fentin acetate, fentin hydroxide, fluazinam, fludioxonil,flumetover (RPA 403397), fluquinconazole, flusilazole, flutolanil,flutriafol, folpet, fosetyl-aluminum, furalaxyl, furametapyr (S-82658),hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane,kasugamycin, kresoxim-methyl, mancozeb, maneb, mefenoxam, mepronil,metalaxyl, metconazole, metomino-strobin/fenominostrobin (SSF-126),myclobutanil, neo-asozin (ferric methanearsonate), oxadixyl,penconazole, pencycuron, probenazole, prochloraz, propamocarb,propiconazole, pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon,quinoxyfen, spiroxamine, sulfur, tebuconazole, tetraconazole,thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil,triadimefon, triadimenol, tricyclazole, trifloxystrobin, triticonazole,validamycin and vinclozolin; nematocides such as aldicarb, oxamyl andfenamiphos; bactericides such as streptomycin; acaricides such asamitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol,dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin,fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; andbiological agents such as Bacillus thuringiensis including ssp. aizawaiand kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, andentomopathogenic bacteria, virus and fungi. Compounds of this inventionand compositions thereof can be applied to plants geneticallytransformed to express proteins toxic to invertebrate pests (such asBacillus thuringiensis toxin). The effect of exogenously appliedinvertebrate pest control compounds of this invention may be synergisticwith the expressed toxin proteins.

[0282] A general reference for these agricultural protectants is ThePesticide Manual, 12th Edition, C. D. S. Tomlin, Ed., British CropProtection Council, Farnham, Surrey, U.K., 2000.

[0283] Preferred insecticides and acaricides for mixing with compoundsof this invention include pyrethroids such as cypermethrin, cyhalothrin,cyfluthrin, beta-cyfluthrin, esfenvalerate, fenvalerate andtralomethrin; carbamates such as fenothicarb, methomyl, oxamyl andthiodicarb; neonicotinoids such as clothianidin, imidacloprid andthiacloprid; neuronal sodium channel blockers such as indoxacarb;insecticidal macrocyclic lactones such as spinosad, abamectin,avermectin and emamectin; γ-aminobutyric acid (GABA) antagonists such asendosulfan, ethiprole and fipronil; insecticidal ureas such asflufenoxuron and triflumuron; juvenile hormone mimics such as diofenolanand pyriproxyfen; pymetrozine; and amitraz. Preferred biological agentsfor mixing with compounds of this invention include Bacillusthuringiensis and Bacillus thuringiensis delta endotoxin as well asnaturally occurring and genetically modified viral insecticidesincluding members of the family Baculoviridae as well as entomophagousfungi.

[0284] Most preferred mixtures include a mixture of a compound of thisinvention with cyhalothrin; a mixture of a compound of this inventionwith beta-cyfluthrin; a mixture of a compound of this invention withesfenvalerate; a mixture of a compound of this invention with methomyl;a mixture of a compound of this invention with imidacloprid; a mixtureof a compound of this invention with thiacloprid; a mixture of acompound of this invention with indoxacarb; a mixture of a compound ofthis invention with abamectin; a mixture of a compound of this inventionwith endosulfan; a mixture of a compound of this invention withethiprole; a mixture of a compound of this invention with fipronil; amixture of a compound of this invention with flufenoxuron; a mixture ofa compound of this invention with pyriproxyfen; a mixture of a compoundof this invention with pymetrozine; a mixture of a compound of thisinvention with amitraz; a mixture of a compound of this invention withBacillus thuringiensis and a mixture of a compound of this inventionwith Bacillus thuringiensis delta endotoxin.

[0285] In certain instances, combinations with other invertebrate pestcontrol compounds or agents having a similar spectrum of control but adifferent mode of action will be particularly advantageous forresistance management. Thus, compositions of the present invention canfurther comprise a biologically effective amount of at least oneadditional invertebrate pest control compound or agent having a similarspectrum of control but a different mode of action. Contacting a plantgenetically modified to express a plant protection compound (e.g.,protein) or the locus of the plant with a biologically effective amountof a compound of invention can also provide a broader spectrum of plantprotection and be advantageous for resistance management.

[0286] Invertebrate pests are controlled in agronomic and nonagronomicapplications by applying one or more of the compounds of this invention,in an effective amount, to the environment of the pests including theagronomic and/or nonagronomic locus of infestation, to the area to beprotected, or directly on the pests to be controlled. Thus, the presentinvention further comprises a method for the control of an invertebratepest in agronomic and/or nonagronomic applications, comprisingcontacting the invertebrate pest or its environment with a biologicallyeffective amount of one or more of the compounds of the invention, orwith a composition comprising at least one such compound or acomposition comprising at least one such compound and an effectiveamount of at least one additional biologically active compound or agent.Examples of suitable compositions comprising a compound of the inventionand an effective amount of at least one additional biologically activecompound or agent include granular compositions wherein the additionalbiologically active compound or agent is present on the same granule asthe compound of the invention or on granules separate from those of thecompound of this invention.

[0287] A preferred method of contact is by spraying. Alternatively, agranular composition comprising a compound of the invention can beapplied to the plant foliage or the soil. Compounds of this inventionare also effectively delivered through plant uptake by contacting theplant with a composition comprising a compound of this invention appliedas a soil drench of a liquid formulation, a granular formulation to thesoil, a nursery box treatment or a dip of transplants. Compounds arealso effective by topical application of a composition comprising acompound of this invention to the locus of infestation. Other methods ofcontact include application of a compound or a composition of theinvention by direct and residual sprays, aerial sprays, gels, seedcoatings, microencapsulations, systemic uptake, baits, eartags, boluses,foggers, fumigants, aerosols, dusts and many others. The compounds ofthis invention may also be impregnated into materials for fabricatinginvertebrate control devices (e.g. insect netting).

[0288] The compounds of this invention can be incorporated into baitsthat are consumed by the invertebrates or within devices such as trapsand the like. Granules or baits comprising between 0.01-5% activeingredient, 0.05-10% moisture retaining agent(s) and 40-99% vegetableflour are effective in controlling soil insects at very low applicationrates, particularly at doses of active ingredient that are lethal byingestion rather than by direct contact.

[0289] The compounds of this invention can be applied in their purestate, but most often application will be of a formulation comprisingone or more compounds with suitable carriers, diluents, and surfactantsand possibly in combination with a food depending on the contemplatedend use. A preferred method of application involves spraying a waterdispersion or refined oil solution of the compounds. Combinations withspray oils, spray oil concentrations, spreader stickers, adjuvants,other solvents, and synergists such as piperonyl butoxide often enhancecompound efficacy.

[0290] The rate of application required for effective control (i.e.“biologically effective amount”) will depend on such factors as thespecies of invertebrate to be controlled, the pest's life cycle, lifestage, its size, location, time of year, host crop or animal, feedingbehavior, mating behavior, ambient moisture, temperature, and the like.Under normal circumstances, application rates of about 0.01 to 2 kg ofactive ingredient per hectare are sufficient to control pests inagronomic ecosystems, but as little as 0.0001 kg/hectare may besufficient or as much as 8 kg/hectare may be required. For nonagronomicapplications, effective use rates will range from about 1.0 to 50mg/square meter but as little as 0.1 mg/square meter may be sufficientor as much as 150 mg/square meter may be required. One skilled in theart can easily determine the biologically effective amount necessary forthe desired level of invertebrate pest control.

[0291] The following TESTS demonstrate the control efficacy of compoundsof this invention on specific pests. “Control efficacy” representsinhibition of arthropod development (including mortality) that causessignificantly reduced feeding. The pest control protection afforded bythe compounds is not limited, however, to these species. See IndexTables A-C for compound descriptions. The following abbreviations areused in the Index Tables which follow: t is tertiary, i is iso, Me ismethyl, Et is ethyl, Pr is propyl, i-Pr is isopropyl, Bu is butyl Theabbreviation “Ex.” stands for “Example” and is followed by a numberindicating in which example the compound is prepared. INDEX TABLE A

Compound R³ R⁴ R⁵(a) R⁵(b) (R⁶)_(q) ¹H NMR 1 (Ex. 1) i-Pr Me H CF₃2-Cl * 2 (Ex. 2) i-Pr Me H CO₂Me 2-Cl * 3 i-Pr Me H CO₂Me 2-Me * 4 i-PrMe H CF₃ 2-Me * 5 i-Pr Me H CF₃ 2-F * 6 t-Bu Me H CF₃ 2-Me * 7 i-Pr MeMe CF₃ 2-Cl * 8 i-Pr Me H CF₃ 2,6-F₂ *

[0292] INDEX TABLE B

Compound R³ R⁴ R⁵ R⁶ ¹H NMR B1 (Ex. 3) i-Pr Me CF₃ 2-Cl *

[0293] INDEX TABLE C Compd. No. ¹H NMR Data (CDCl₃ solution unlessindicated otherwise)^(a) 1 9.4(bs, 1H), 7.6 − 7.5(d, 1H), 7.4 − 7.1(m,6H), 5.8(bd, 1H), 5.4(dd, 1H), 4.3 − 4.1(m, 1H), 3.6 − 3.4(m, 2H),1.84(s, 3H), 1.3 − 1.2(m, 6H). 2 9.4 − 9.3(bs, 1H), 7.6(d, 1H), 7.4 −7.3(d, 1H), 7.3 − 7.0(m, 5H), 5.8(d, 1H), 5.5(dd, 1H), 4.2 − 4.1(m, 1H),3.89(s, 3H), 3.7 − 3.4(m, 2H), 1.81(s, 3H), 1.3 − 1.2(m, 6H). 3 twoisomers: 9.5 + 9.3 − 9.2(2 × bs, 1H), 7.3 − 7.0(m, 7H), 5.8(bm, 1H), 5.1− 5.0(m, 1H), 4.1 − 4.0(m, 1H), 3.87(s, 3H), 3.7 − 3.5(m, 1H), 3.5 −3.3(m, 1H), 2.5(2 × s, 3H), 2.0 − 1.9 + 1.87(2 × s, 3H), 1.3 − 1.1(m,6H). 4 (DMSO-d₆) 9.81(s, 1H), 8.1 − 8.0(m, 1H), 7.3 − 6.9(m, 7H), 5.3(m,1H), 4.0 − 3.9(m, 1H), 3.6(m, 1H), 1.79(s, 3H), 1.1(m, 6H). 5 (DMSO-d₆)9.85(s, 1H), 8.1 − 8.0(d, 1H), 7.4 − 6.9(m, 7H), 5.5 − 5.4(m, 1H), 4.0 −3.9(m, 1H), 3.7(m, 1H), 3.5 − 3.3(m, 1H), 2.07(s, 3H), 1.11(d, 3H),1.06(d, 3H). 6 (DMSO-d₆) 9.3 − 9.2(s, 1H), 7.4 − 7.0(m, 7H), 5.8(d, 1H),5.1 − 5.0(m, 1H), 3.6 − 3.3(m, 2H), 1.88(s, 3H), 1.40(s, 9H). 7 10.0 −9.9(s, 1H), 7.5 − 7.1(m, 7H), 5.9(d, 1H), 4.2 − 4.1(m, 1H), 3.7(d, 1H),3.3 − 3.2(d, 1H), 2.27(s, 3H), 1.50(s, 3H), 1.3 − 1.2(m, 6H). 8 9.3(s,1H), 7.3 − 7.2(m, 3H), 7.0(m, 3H), 5.8(d, 1H), 5.0 − 4.9(dd, 1H), 4.1(m,1H), 3.7 − 3.4(Abd, 2H), 2.10(s, 3H), 1.3 − 1.1(m, 6H). B1 9.6(s, 1H),7.6 − 7.1(m, 7H), 5.9 − 5.8(d, 1H), 5.0 − 4.9(dd, 1H), 4.8 − 4.7(m, 1H),4.3(dd, 1H), 4.2 − 4.1(m, 1H), 2.10(s, 3H), 1.3 − 1.2(m, 6H).

BIOLOGICAL EXAMPLES OF THE INVENTION Test A

[0294] For evaluating control of diamondback moth (Plutella xylostella)the test unit consisted of a small open container with a 12-14-day-oldradish plant inside. This was pre-infested with 10-15 neonate larvae ona piece of insect diet by use of a core sampler to remove a plug from asheet of hardened insect diet having many larvae growing on it andtransfer the plug containing larvae and diet to the test unit. Thelarvae moved onto the test plant as the diet plug dried out.

[0295] Test compounds were formulated using a solution containing 10%acetone, 90% water and 300 ppm X-77® Spreader Lo-Foam Formula non-ionicsurfactant containing alkylarypolyoxyethylene, free fatty acids, glycolsand isopropanol (Loveland Industries, Inc.), unless otherwise indicated.The formulated compounds were applied in 1 mL of liquid through a SUJ2atomizer nozzle with ⅛ JJ custom body (Spraying Systems Co.) positioned1.27 cm (0.5 inches) above the top of each test unit. All experimentalcompounds in these tests were sprayed at 250 ppm (or lower) andreplicated three times. After spraying of the formulated test compound,each test unit was allowed to dry for 1 hour and then a black, screenedcap was placed on top. The test units were held for 6 days in a growthchamber at 25° C. and 70% relative humidity. Plant feeding damage wasthen visually assessed based on foliage consumed.

[0296] Of the compounds tested the following provided excellent levelsof plant protection (ratings of 0-1, 10% or less feeding damage): 1*, 3,4*, 5*, 6*, 7*, 8**.

Test B

[0297] For evaluating control of fall armyworm (Spodoptera frugiperda)the test unit consisted of a small open container with a 4-5-day-oldcorn (maize) plant inside. This was pre-infested (using a core sampler)with 10-15 1-day-old larvae on a piece of insect diet.

[0298] Test compounds were formulated and sprayed at 250 ppm (or lower)as described for Test A. The applications were replicated three times.After spraying, the test units were maintained in a growth chamber andthen visually rated as described for Test A.

[0299] Of the compounds tested, the following provided excellent levelsof plant protection (10% or less feeding damage): 1*, 4**, 5*.

Test C

[0300] For evaluating control of tobacco budworm (Heliothis virescens)the test unit consisted of a small open container with a 6-7 day oldcotton plant inside. This was pre-infested (using a core sampler) with 82-day-old larvae on a piece of insect diet.

[0301] Test compounds were formulated and sprayed at 250 ppm (or lower)as described for Test A. The applications were replicated three times.After spraying, the test units were maintained in a growth chamber andthen visually rated as described for Test A.

[0302] Of the compounds tested, the following provided very good toexcellent levels of plant protection (20% or less feeding damage): 1*,4**, 5*, 6*.

Test D

[0303] For evaluating control of beet armyworm (Spodoptera exigua) thetest unit consisted of a small open container with a 4-5-day-old cornplant inside. This was pre-infested (using a core sampler) with 10-151-day-old larvae on a piece of insect diet.

[0304] Test compounds were formulated and sprayed at 250 ppm (or lower)as described for Test A. The applications were replicated three times.After spraying, the test units were maintained in a growth chamber andthen visually rated as described for Test A.

[0305] Of the compounds tested, the following provided very good toexcellent levels of plant protection (20% or less feeding damage): 1*,4*, 5*, 6*.

What is claimed is:
 1. A compound of Formula I, and N-oxides oragriculturally suitable salts thereof

wherein A and B are independently O or S; J is an optionally substituted5- or 6-membered nonaromatic heterocyclic ring; K is taken together withthe two contiguous linking carbon atoms to form a phenyl ring or a 5- or6-membered heteroaromatic ring, each ring optionally substituted; R¹ isH; C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl, eachoptionally substituted; C₂-C₆ alkylcarbonyl; C₂-C₆ alkoxycarbonyl; C₂-C₆alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl; R² is H, C₁-C₆ alkyl,C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy, C₁-C₄alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆alkoxycarbonyl or C₂-C₆ alkylcarbonyl; R³ is H; G; C₁-C₆ alkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, each optionally substituted;or R² and R³ can be taken together with the nitrogen to which they areattached to form a ring containing 2 to 6 atoms of carbon and optionallyone additional atom of nitrogen, sulfur or oxygen, and said ring may beoptionally substituted; and G is an optionally substituted 5- or6-membered nonaromatic carbocyclic or heterocyclic ring, optionallyincluding one or two ring members selected from the group consisting ofC(═O), SO or S(O)₂.
 2. The compound of claim 1 of Formula Ia

wherein A and B are independently O or S; J is

K is taken together with the two linking atoms to form a phenyl ring ora 5- or 6-membered heteroaromatic ring, each ring optionally substitutedwith from 1 to 4 R⁴; X is O or S; R¹ is H; or C₁-C₆ alkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substitutedwith one or more substituents independently selected from the groupconsisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio,C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₁-C₄alkylamino, C₂-C₈ dialkylamino and C₃-C₆ cycloalkylamino; or R¹ is C₂-C₆alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl or C₃-C₈dialkylaminocarbonyl; R² is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylamino, C₂-C₈dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkoxycarbonyl or C₂-C₆alkylcarbonyl; R³ is H; G; C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl,C₃-C₆ cycloalkyl, each optionally substituted with one or moresubstituents independently selected from the group consisting ofhalogen, G, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₆alkoxycarbonyl, C₂-C₆ alkylcarbonyl, C₃-C₆ trialkylsilyl, or a phenyl,phenoxy or 5- or 6-membered heteroaromatic ring, each ring optionallysubstituted with one to three substituents independently selected fromR⁶; C₁-C₄ alkylamino; C₂-C₈ dialkylamino; C₃-C₆ cycloalkylamino; C₂-C₆alkoxycarbonyl or C₂-C₆ alkylcarbonyl; or R² and R³ can be takentogether with the nitrogen to which they are attached to form a ringcontaining 2 to 6 atoms of carbon and optionally one additional atom ofnitrogen, sulfur or oxygen, said ring may be optionally substituted withfrom 1 to 4 substituents selected from R⁷; G is a 5- or 6-memberednonaromatic carbocyclic or heterocyclic ring, optionally including oneor two ring members selected from the group consisting of C(═O), SO orS(O)₂ and optionally substituted with from 1 to 4 substituents selectedfrom R⁷; each R⁴ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, hydroxy, C₁-C₄alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆cycloalkylamino, or C₃-C₆ trialkylsilyl; or each R⁴ is independentlyphenyl, benzyl or phenoxy, each optionally substituted with from one tothree substituents selected from R⁶; each R⁵ is independently H, C₁-C₆alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl,C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN,CO₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈dialkylaminocarbonyl, C₃-C₆ trialkylsilyl or W; (R₅)₂ when attached toadjacent carbon atoms can be taken together as —OCF₂O—, —CF₂CF₂O—, or—OCF₂CF₂O—; each W is independently a phenyl, benzyl, benzoyl, phenoxy,5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or10-membered fused heterobicyclic ring system, each ring optionallysubstituted with from one to three substituents independently selectedfrom R⁶; each R⁶ is independently C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl,C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆(alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl;each R⁷ is independently C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂ alkoxy;m is an integer from 1 to 7; and n is an integer from 1 to
 3. 3. Thecompound of claim 2 wherein K is taken together with the two linkingatoms to form a phenyl ring optionally substituted with 1 to 3 R⁴. 4.The compound of claim 2 wherein K is taken together with the two linkingatoms to form a thiophene, pyrazole, isoxazole, pyridine or pyrimidineoptionally substituted with 1 to 3 R⁴.
 5. The compound of claim 3 orclaim 4 wherein A and B are both O; n is 1 or 2; R¹ is H, C₁-C₄ alkyl,C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₂-C₆ alkylcarbonyl orC₂-C₆ alkoxycarbonyl; R² is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄alkynyl, C₃-C₆ cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;R³ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆cycloalkyl optionally substituted with one or more substituents selectedfrom the group consisting of halogen, CN, C₁-C₂ alkoxy, C₁-C₂ alkylthio,C₁-C₂ alkylsulfinyl and C₁-C₂ alkylsulfonyl; one of the R⁴ groups isattached to the K ring at one of the two positions ortho to the twolinking atoms, and said R⁴ is C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen, CN,NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄haloalkylsulfinyl or C₁-C₄ haloalkylsulfonyl; each R⁵ is independentlyH, C₁-C₄ alkyl, C1-C₄ haloalkyl, halogen, CN, NO₂, C₁-C₄ haloalkoxy,C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl or C₂-C₄alkoxycarbonyl; and one R⁵ is optionally W; and W is a phenyl ring or a5- or 6-membered heteroaromatic ring, each ring optionally substitutedwith one to three substituents independently selected from R⁶.
 6. Thecompound of claim 5 wherein J is J-36;

R¹ is H; R² is H or CH₃; R³ is H; or C₁-C₄ alkyl, C₁-C₄ alkenyl or C₁-C₄alkynyl, each optionally substituted with halogen, CN, OCH₃,S(O)_(p)CH₃; each R⁴ is independently CH₃, CF₃, CN or halogen, and oneR⁴ group is attached to the K ring at the atom adjacent to the NR¹C(═A)Jmoiety; R⁵ is H, C₁-C₄ alkyl, C₁-C₄ haloalkyl, or W; W is

V is N, CH, CF, CCl, CBr or CI; each R⁶ and R⁸ is independently H, C₁-C₆alkyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, halogen, CN, C₁-C₄ alkoxy,C₁-C₄ haloalkoxy or C₁-C₄ haloalkylthio; m is 1 or 2; and p is 0, 1 or2.
 7. The compound of claim 6 wherein V is N.
 8. The compound of claim 6wherein V is CH, CF, CCl or CBr.
 9. The compound of claim 5 wherein J isJ-37;

R¹ is H; R² is H or CH₃; R³ is H; or C₁-C₄ alkyl, C₁-C₄ alkenyl or C₁-C₄alkynyl, each optionally substituted with halogen, CN, OCH₃,S(O)_(p)CH₃; each R⁴ is independently CH₃, CF₃, CN or halogen, and oneR⁴ group is attached to the K ring at the atom adjacent to the NR¹C(═A)Jmoiety; R⁵ is H, C₁-C₄ alkyl, C₁-C₄ haloalkyl, or W; W is

V is N, CH, CF, CCl, CBr or CI; R⁶ is independently H, C₁-C₆ alkyl,C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, halogen, CN, C₁-C₄ alkoxy, C₁-C₄haloalkoxy or C₁-C₄ haloalkylthio; R⁹ is H, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃C₆ alkynyl or C₃-C₆haloalkynyl; m is 1 or 2; and p is 0, 1 or
 2. 10. The compound of claim1 selected from the group consisting of1-(2-Chlorophenyl)-4,5-dihydro-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-trifluoromethyl)-1H-pyrazole-5-carboxamide,Methyl1-(2-chlorophenyl)-4,5-dihydro-5-[[[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]amino]carbonyl]1H-pyrazole-3-carboxylate,Methyl4,5-dihydro-5-[[[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]amino]carbonyl]-1-(2-methylphenyl)-1H-pyrazole-3-carboxylate,4,5-Dihydro-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(2-methylphenyl)-3-(trifluormethyl)-1H-pyrazole-5-carboxamide,1-(2-Fluorophenyl)-4,5-dihydro-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,N-[2-[[(1,1-Dimethylethyl)amino]carbonyl]-6-methylphenyl]-4,5-dihydro-1-(2-methylphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide, and1-(2,6-Difluorophenyl)-4,5-diydro-N-[2-methyl-6-[[1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide.11. A method for controlling an invertebrate pest comprising contactingthe invertebrate pest or its environment with a biologically effectiveamount of a compound of claim
 1. 12. The method of claim 11 furthercomprising a biologically effective amount of at least one additionalcompound or agent for controlling an invertebrate pest.
 13. Acomposition for controlling an invertebrate pest comprising abiologically effective amount of a compound of claim 1 and at least oneadditional component selected from the group consisting of surfactants,solid diluents and liquid diluents.
 14. The composition of claim 13further comprising an effective amount of at least one additionalbiologically active compound or agent.